The Winchester Inn

On our third trip to the Oregon Shakespeare Festival in Ashland, we gave the Winchester Inn a try. And as long as they have availability, this will be our home away from home every year. Little treats in your room every afternoon; amazing breakfasts. Can't rave about the dinners because we couldn't get a reservation. Next time we'll plan ahead. Close to the festival. A definite winner!

We booked our reservation at the Winchester and I have to admit the room, the service, and the food all exceeded our expectations. The staff is helpful and friendly and the room was gorgeous. Breakfast was a delight, even though I could barely finish it most days. I can't wait to go back to Ashland, because I know exactly where I will be staying!

Great food and bar, superb breakfasts, always service with a smile and the beds can't be beat. Relax in the gardens with wine and cheese or read your morning paper with a second cup of coffee.

A perfect spot for a mini-vacation. Staff was attentive and the setting is grand. Especially nice to sit and overlook the garden.

My wife and I have been staying at the Winchester Inn for nearly 20 yrs. We always look forward to it. Mike and Lorie are great hosts. The staff is great.

The Winchester is a two-minute walk to theatres, park, and the heart of town. Owned and operated by the wonderful Gibbs family for decades, the Inn offers unparalleled charm and comfort with individual balconies and/or patios on most rooms, lots of nooks and crannies on the landscaped property for reading and relaxing, a wonderful onsite restaurant, and the coziest bar in town. The only drawback is that the Winchester is no secret - during high season it is booked very early.

The Winchester Inn has become our favorite place to stay when we are in Ashland. The people working there are always sweet and 'at your service!' No attitude problem at this B&B. The two things I love the most is the breakfast and the charming wine bar. I usually stay there in the off season when the prices are less and I can pick the room I want without trouble. This works for me because I'm unable to visit during the summer and busier months anyway. Everyone is friendly and the atmosphere is cozy, charming and comfortable in every way. Close walking distance to everything in Ashland. No getting in the car when you stay here. That's a big plus for me!

From the warm greeting at check-in to quickly accommodating a to-go breakfast need, the front of the house staff at Winchester Inn provided excellent service. All our encounters with the front desk and bar/restaurant staff were personable and pleasant. This aspect was a highlight of our stay. While we did not partake of dinner at the inn, Drew and his bartender partner have put together the longest and most comprehensive cocktail menu we have ever seen! We enjoyed chatting with them one night at the bar and learning about their cocktails and process. The other aspects of our stay were fine, but not necessarily memorable. Winchester Inn really feels more like a small hotel than bed and breakfast, so guests who prefer one type of lodging over the other may want to note that. We stayed in the Garden Room, located at the top of the stairs from the main reception area. The bedding is soft and plush. The shower and water closet share a space that has been recently renovated. The window seat was a picturesque addition with the view of the garden and trees. In a historic building, maintenance and refurbishment are always an ongoing process, and with that in mind the room could use some minor help, such as the carpet looked stained and worn in places and wallpaper was peeling in some corners. None of these things interfered with our stay, and are all things that I am confident management is already familiar with given previous reviews and comments on TripAdvisor. If such things are something that might bother you as a future guest, I would just suggest looking into reserving a different room type, perhaps one that has been more recently touched overall in their maintenance plan. The owners and staff aim to please, so let them help guide you to which room might be the best fit. For guests who are interested in being in the center of town life near the Shakespeare Festival, and having dining on-site, this is probably a place you will want to consider.

Great location, great staff, great food and great rooms - can't ask for much more!

We had another memorable stay. Service and food were great as usual.

We were in Ashland and needed a place to stay for the night. We chose the Queen Anne room because it has two beds. The beds were very clean and comfortable. The shower was amazing and the rest of the bathroom was also very clean. I wish I could have stayed longer.

For we locals, off season is the best way to indulge and still get a great deal. So close to so much. No need to drive as the Cabaret Theatre is right around the corner.

What a wonderful experience. The staff is incredibly helpful and friendly, the rooms were great and the lounge and restaurant were first rate. It reminded me very much of being in a country hotel in France. I will be back again and again.

We stayed in the Sunset room that had a beautiful balcony that would be wonderful in a different season! While the room itself was lovely, it is worth noting we heard quite a bit of noise below us that led us to believe that we must have been above the kitchen. We are early-birds, so it didn't bother us that much. Although we did have to stick a pamphlet in the window pane to keep the glass from rattling from what we presumed was the vibrations from the kitchen exhaust fan...gotta love old windows! Breakfast was wonderful and the service impeccable. Overall, we really did enjoy our stay and would be happy to return!

Feather-bed,fresh ground coffee,in the fridge,two person jetted tub that was actually big enough for two,a welcome to the Inn treat in the afternoon,a beautifully lit gazebo and garden area at night,outstanding dinner and drinks with a book for the wine list.All this and an included breakfast.Excellent location to shopping and the night life.

This is a great place to stay if you are in the Ashland area. Fabulous rooms, terrific staff and breakfasts that set you up for the day. If you have not stayed at the Winchester put it on your to do list for 2013.

Beautiful accommodations...incredible breakfast...a fantastic experience!

Frienly personell. Especially, Great Thanks to administrator Rebecca, who was so nice!

Clean, comfortable, with extremely attentive staff dedicated to providing excellent service

We stopped here as part of a honeymoon trip up through Oregon wine country! The best stop by far! Wonderful accommodations, fantastic food! Great experience overall! Would definitely recommend and revisit this gem in Oregon!

For those of you who love Downton Abbey, now is your opportunity to live the dream. Of all the B&Bs that my wife and I have had the pleasure to stay in, this one has more character, ambiance, service, and value than any of the others. We listened to incredible music, played live in their small wine bar; reveled in their comfortable rooms and spent a delightful time in the hip and historic town of Ashland. The breakfast was fantastic. I don't know how they make any money and serve a breakfast like that for free. We will return as often as possible.

Traveling with young children during the holidays creates a lot of worries but Ashland is a wonderful place to stop when travelling from california to oregon. The Winchester Inn's suites are well appointed and with enough room for the kids to stretch out. The breakfast is also excellent - they have a chef on duty just like you would hope for such a beautiful Victorian B&B just downtown in a beautiful small town.

It was hard to leave the Inn and go out to enjoy Ashland with all of the wonderful homeyness of our room. We had a guestroom first and thought our luck was extraordinary. When we asked for an extra night and found we needed to move to a suite in the next house over, we were feeling some trepidation until we saw the new digs. The bed was even more plush, the bathroom 4 times more luxurious and a super cute little sitting room. We never wanted to leave.

We spent 3 nights during the week of Thanksgiving at the Winchester Inn and enjoyed every second of it. Since it was during their low season, the rates were amazing. Our 2-room suite was large and beautifully decorated. We felt comfortable and right at home the minute we entered the suite. The breakfasts at the Winchester Inn were gourmet and absolutely delicious and served by a charming and efficient staff. We have no complaints about our stay and will definitely return.

There's only one word that wraps up ourexperience at the Winchester: Fantastic!!!

Very nice B & B. Wonderful breakfasts and great service! Location can't be beat.

We always feel at home when staying here. We are welcomed and recognized. Everyone is helpful without being intrusive. The food is always great and the bar is comfortable and friendly.

We stay at the Winchester at least once evry year. It is one of the highlightes of our Ashland trips.

It is always a joy to stay here; the room was just what we expected, as we are return guests. The dinner was superb. We walk everywhere and actually have no need of a car in Ashland because the Winchester is so close to everything. We will be back next year.

We have had wonderful dinners here for 20+years. This was our first week-end stay and it was delightful. Highly recommended.

The Winchester Inn has the best food in Ashland. We have tried all of the good restaurants in Ashland and Breakfast and Dinner at the Winchester is far superior to any other. Everything at the Winchester inn is a winner!!! The rooms are lovely, the gardens peaceful for reading or relaxing and the evening pastries you find in your room are divine!

Very nice B&B, comfortable. great location, would definitely stay there again!

This was at least our fourth if not fifth stay at the Winchester Inn. In fact, we only stay there when visiting Ashland. Management is highly professional and attentive but not smothering. The rooms are always clean and in good repair and comfortably furnished. The included breakfast is always ample and reflective of interesting cooking; there's something for everyone's taste (we have never had dinner at the Winchester but have eaten in bar/bistro and thoroughly enjoyed the faire). Another nice attribute is the inn's grounds where on any sunny day it's nice to sit in the gazebo and read or simply relax. Finally, the Winchester's location is perfectly situated downtown for walking about (four blocks walking to the Shakespeare Festival grounds) yet the inn is not on the busy and sometimes congested main street that runs through downtown. All in all, a first rate lodging experience. LJR, Lake Oswego, OR

We always enjoy our stay here. We had a wonderful dinner (lobster), apps (crab cakes) and were seated in a beautiful alcove in the garden - can't get any better than that. Also very nice berry margaritas. The breakfasts were very well done as always (and I'm a severe critic of food). Very nice dinner service. At breakfast I would like to see coffee refilled without needing to go find some - cream also. Another negative this stay: our bathroom and wine glasses were not changed for clean ones when our room was cleaned. I found another housekeeper, who reluctantly agreed to take them and bring us clean ones (it wasn't her room to clean). One of these clean wine glasses had lipstick all around the top. Also we had to ask someone to bring a second patio chair so we could use the patio outside our door. These are all minor things. It just seems they should be taken care of at this level of lodgings. Additional positives: it's very pleasant to have the ice bucket filled and waiting in one's room in the afternoon. We also enjoy the little sweet treats left under the glass bell. We will certainly come again next year.

A short walk to the theaters and to Lithia Park. The staff is marvelous, rooms are nice and the dining is wonderful.

We had a wonderful stay at the Winchester Inn and hope to repeat the experience in years to come.

The only problem was being hit by the waiter with the swinging door coming out of the kitchen. I suggest putting some windows in those swinging kitchen doors so that any of your staff can see who is walking in that hallway on the way to the restrooms. Thank you.

This is the second time we have stayed at the Winchester Inn and once again it exceeded all of our expectations. The staff are friendly and the service is impeccable. We will definitely be back.

The exquisite dinners were a fabulous surprise, and only added to the wonderful memories we'll treasure from our three nights with the Winchester Inn family. The chef's unique creativity resulted in daily culinary surprises, which included great breakfasts. Will Shakespeare would likely have chosen Winchester Inn to enjoy after a full day's work at the Festival.

Perfect location. Beautifully appointed rooms. Friendly, capable staff. Superb dining & wine list.

We stayed in Ender's room this summer on our second stay at The Winchester Inn. Very nice decor and very clean. My wife and I slept on the King bed. Our 8-year-old slept on the twin that is in the room and then they brought in a portable twin for our 3-year-old. They set the portable up around 6:30. There's not a lot of room once that was set up but there isn't a ton of room anyway. It appeared as though the regular A/C was out and they set up a portable one in the room that probably took up some of the space the portable twin would normally occupy if you have 4 in the room. Thank goodness for the backup A/C though because it was hot. There is a little porch outside with a table and two chairs. Nice for enjoying some wine as you sit outside in the courtyard where white Christmas lights decorate some of the trees. Wine bar was awesome and the breakfast was great! Breakfast comes with the room charge but they give you a receipt at the end telling you how much it was. Our amount for two adults and two children was around $70. Service all around is fantastic. Location is perfect. It's just blocks from the park and the Shakespeare Festival. Having young children we don't go to the Shakespeare Festival. It is also a block away from the main street and all the shops and restaurants. So, you don't need to drive anywhere. It's just a little pricey compared to what you might get elsewhere. They charge $30 more per night for each child over 8. I don't believe my 8-year-old ate $30 worth of breakfast or that his presence in the room amounted to that amount as I would hope they would change the sheets on the twin anyway. But I assume it's pricey because it is peak season, it's centrally located in the heart of downtown Ashland and it is very nice. The price just makes us think long and hard about staying there one night versus two nights.

Our stay at the Winchester Inn was extremely pleasant. The staff was friendly and welcoming, made us feel at home. Our room, one of the smaller ones the inn offers, was spacious and comfortable, full of light, with window seat and couch great for reading. Yet the grounds drew us outside, where the gazebo and other well-placed seating arrangements offered chairs and small tables for relaxing, surrounded by the well-kept garden. Breakfast was a sparkling attraction, with delicious and creative offerings. The wine bar was another much-appreciated feature, providing knowledgeable insights into local wines and scrumptious appetizers. There were also little touches such as the in-room sweet treats which mysteriously appeared each afternoon. The location was also very convenient, being two blocks away from the Shakespeare theaters. When we return to Ashland we will definitely stay here again.

It has been many years since we had a theater vacation in Ashland. We were the winners of a prize given by our local theater in a drawing which was donated by the Winchester Inn. The weather was extremely hot during our stay ranging from 95 to 98 degrees but the Winchester with its many shaded outdoor areas and extremely effective indoor air conditioning made our stay most pleasant. We saw four shows while there and enjoyed all of them. Our room was like home as we sleep in a large four poster bed each night and our house although not as old is elegantly appointed. We enjoyed our stay very much but would like to point out that your personnel were outstanding, taking care of all our needs in an efficient and friendly manner.

The Winchester Inn is a great place to stay while visiting Ashland. The people are very friendly and helpful. The breakfast was fabulous. Great location, easy walk to restaurants and plays.

What a remarkable place. We will definitely return. Your staff was full of hospitality and smiles. We have recommended you to at least a dozen people so far. Riberals

This was a very wonderful experience, with a delightful room, special homemade blackberry mini-tarts in the room for a quick afternoon pick-me-up and excellent restaurant. The room even included high quality wine glasses and corkscrew for those who found bottle on their excursions. The chef is excellent, the wine and beer selections outstanding, and the attentiveness to detail impressive. They even brought a wine chiller to cool the last of a bottle of specialty beer, so it could be served at the proper temperature. Is located next to Paddy's bar, for those who also want an excellent local pub to visit.

My wife and I have stayed at the Winchester for the past decade. We attend the Shakespeare Festival at various times of the year. This Bed and Breakfast is far and away the finest in the area. We have NEVER been disappointed in all the years we have been going there. I cannot recommend The Winchester, and it's excellent management and staff (All the way through to the cleaning services), highly enough.

The Winchester never disappoints. We've been going there for years now, and it remains our first choice among Ashland's many fine B&Bs. Spotless rooms, impeccable service from a friendly and solicitous staff, fine meals in the dining room. Must I cavil? Well, the climb up the hill to the front door is a bit of a trudge, but even that is no trouble in light of what awaits when you get there.

Our favorite place to stay in Ashland continues to please. The stellar staff, terrific food and perfect location give the visitor all the options you need.

We were driving through a rain and snow storm before arriving at the inn, just in time to get a nice dinner at a restaurant next door. The room was clean and comfortable. The breakfast in the morning was superb. We'll have to try dinner at the inn next time since it was not open during the winter (during our visit).

For many years now, we have been meeting friends at the Winchester Inn and taking in the OSF plays - a marvelous mix of friendship and brain candy. And the Winchester staff is always so accommodating - setting a big breakfast table and letting us linger until the chatter stops. This inn maintains its high standards and this year we felt the breakfasts were even better than in the past. The wine bar is very fun too and the rooms are charming with all the amenities needed for a comfortable stay.

the best of the 4 Dinner ,breakfest eveything was perfect

My husband and I stayed here July 11-12, 2012. We go to Ashland once a year and have stayed at most of the B&B's in town. Since we discovered the Winchester, it's has been our favorite of all. The super friendly people that run the beautiful inn, the enjoyable wine bar, the location, the rooms and the fantastic breakfast are all you need to get hooked.

Arrived rather tired after the long drive. Our first impression was at check in and the young woman was not too helpful. Brusque in her responses as apparently I asked too many questions. So we started our stay rather grumpy. Only took one day and due to all the staff & owners we interacted with our attitude changed and continued to improve. We were quite content and knew we made a good choice. Close to everything -the theater, Lithia Park, downtown area etc. Walked everywhere! We intend to stay there again when we return to Ashland. Thank you.

Based on a 2 night stay in the Sylvan room, our only visit to the Winchester Inn. Very highly recommended, in town, walkable to lot of things, lovely rooms, staff, amenities, garden and restaurant. Price is the only downside, but worth the price if you want a comfortable luxurious stay.

My husband and I stayed in the Sunset room and loved it! It was one of the smaller rooms in the B&B but had so much to offer...including a private balcony with a breathtaking view! The staff were both kind and helpful. Every morning we enjoyed a delicious breakfast downstairs. We miss it already and will be returning! I wouldn't hesitate to recommend this B&B.

Most people who stay here are long time guests and also subscribers to the Oregon Shakespeare Festival. The owners are exceptionally friendly making every effort to treat you as family. Their warmth and attention to detail makes The Winchester Inn a second home. Breakfast is as good as you can imagine with choices to please everyone. The dinner is over the top and if combined with their breakfast, the five star food is more than you need. Their bar is also a wonderful place to sit and unwind. Most of the guests are as friendly as the owners so it is a wonderful place to meet people with similar interests. After many years of going there, we will be returning in August for a week.

This inn is great on on fronts and we will return at every opportunity

This INN in Ashland Oregon is beyond belief! Everything we wanted was at a finger tip ! You have a delicious restaurant with unbelievable service. Our entire stay was like a dream ! Thank you all.

What a wonderful find. We walked to a performance of the Oregon Cabaret and could have walked to any of the local theatres and restaurants. We'll be back!

Close to everything. Wonderful breakfasts--the best I've ever had at a B&B. Friendly staff who get to know your preferences. Comfortable and spacious rooms. I couldn't ask for anything more from the Winchester Inn. I just loved it and would go back again and again.

Arrived at the Winchester Inn after a long flight from Houston. The reception was warm and welcoming and the room was comfy and inviting. After a quick wash-up, we were off to a fantastic dinner at the Inn and then a show at the neighboring Cabaret Theatre. Such a great way to end the year and begin a new one.! Will definitely stay again, and again, and . . .

We arrived late so instructions for getting our keys were taped to the door - no problem. However, our welcome letter included information about breakfast the next day. We arrived at breakfast to find out that the restaurant is closed at this time of the year. Bad communication resulted in disappointment and an early check out!

Overall our stay on our wedding night was fantastic with only 2 issues, the neighbors alarm clock started at 2am and went off at 6am. The other issue was the kitchen was closed for breakfast and we weren't made aware of this at the time of our reservations. Other then this, we will be back and hopefully we can have breakfast this time :) C.W.

Overnight getaway for 18 year old daughter and mom- Gorgeous inn- kind keepers- the most amazing food of our lives!!!! Dinner the night of our arrival was perfect, we couldn't have dreamed up a better meal the combinations of edible art and unbeatable flavor will be a favorite memory for years to come- Complimentary breakfast!!! Goodness gracious what a Devine way to start the day- everything about the Winchester inn makes me want a repeat but the food will make it priority- Incredible service & unbelievable chef in a beautiful, intimate location.

Beautiful room, AMAZING dining experience! Wonderful experience!

The staff and accommodations could not have been more perfect. We had a wonderful Thanksgiving weekend at the Winchester and will be returning.

The room was so clean and tasteful. It was close to downtown and Lithia Park plus the breakfast was delicious.

There's a reason people come back again and again to the Winchester Inn. The rooms and beds are wonderful and beautiful, the staff is always so nice and the breakfasts are nothing short of amazing. I've tried 1 other B&B and 2 hotels in Ashland and were disappointed in both. All 5 of my stays at the Winchester have been a 5 star experience. I'll be back!

My husband and I really enjoyed our stay. Everyone was very nice. The room was spacious and clean. The location was perfect, right off the main street. We ate dinner here and the food was great, as was the service. The only drawback I suppose is the cost- not super cheap, but that is Ashland for ya!

The location is great. The staff was very friendly. The room was a little tired looking (I know this is an old structure but the rooms/baths could use a bit of updating). I thought the price was a bit too high.

Your breakfasts were exceptional! The service was excellent, the ambiance was lovely, the food was delicious and plentiful. My room was nice, but next time I would probably choose a larger room.

This is the second time we have stayed at the Winchester Inn and we love it. The atmosphere is relaxing and the staff, accomodations and food are wonderful. It also has an excellent location for exploring Ashland.

We had a very pleasant stay in The Winchester Inn. Although our room was quite small we had the luxury of a balcony to use. The addition of great weather and a great view of the Milky Way each night made our stay. The girl who arrived for the turn down service and ended up helping me to unravel my jewellery was a delight. Breakfast was delicious, I am still thinking about french toast with a strawberry compote and banana cream...........

This was our third visit to Winchester Inn, and it once again reinforced why it is our favorite place to stay in Ashland. Close to everything....just leave your car and walk to the theaters. Really nicely appointed rooms, fresh air and good air conditioning when you need it. Best of all, the food has gotten even better. Breakfasts are fantastic (be sure to try the poached egg special at least once!). Really nice people; we will be back for sure.

I recently spent four nights in the Catherine M. Room at the Winchester Inn. Although the room is one of the lower priced rooms at this convenient location, it is exceptionally well-designed and comfortable . The room shares a balcony with another room and the bathroom, closet and storage space were all spacious. The service far exceeded our expectations . It is clear the owners and all those who work at the Winchester Inn place a high priority of anticipating and responding to the needs and wishes of their guests.

This is the best place to stay in Ashland. We have been coming here for years. The service, food, rooms--all outstanding! Highly recommended!

We loved our two nights at the Winchester. It's location is excellent for seeing plays and just wandering about town. The breakfasts were outstanding! We did not eat dinner there, but our room was lovely, peaceful, and spacious.

Beautiful room. Quiet. Attentive service. Wonderful breakfasts. Great location.

within an easy walk to theaters, shops, most restaurants. Pricey but worth it.

We spent one night at the Winchester with 2 children as a stop on our way home from a long road trip. We found the Inn to be peaceful, well appointed, and a good value as far as B&Bs go. The breakfast was superb. My wife and I plan to return by ourselves for a weekend next Spring. While good for our family, we think it will be even better as a getaway for the just the two of us.

There was apparently a wasp(?) nest beneath the window of my room from which there was constant flying traffic at least during the day. This was a little disconcerting and made me reluctant to open my window and enjoy the fresh air.

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I am sorry that the bees unsettled you. There is indeed a beehive located in the front of the building. It has been there for decades. I hope that you spoke with the front desk as we do have window screens available so that you can enjoy the fresh air without nature becoming intrusive. We have yet to have a guest stung by one of the bees, and decided that the best course of action is to leave them alone. We continue to appreciate them because of our gardens. We would be happy to move you to another room for the future! Regards, Drew Gibbs

Awesome place to stay. Walking distance to Shakespeare plays. Great dining experience dinner and breakfast. Friendly and helpful staff. Stayed in the Barbara Howard suite very relaxing.

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I am so thrilled to hear that you enjoyed you stay. I hope we see you again soon! Regards, Drew Gibbs

Excellent stay at the Winchester Inn.... Everyone was very nice!!!!

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I know that the staff takes great pride in being able to offer the amenities and service that we provide. Thanks for letting them know you appreciate it! Regards, Drew Gibbs

Had a lovely respite at the Winchester Inn on our travels back up to Seattle. We were in the Sunset room and enjoyed sitting out on the deck and the view.

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Thank you so much for joining us! We can't wait to have you back! Regards, Drew Gibbs

This inn is a couple of blocks from the Shakespeare Festival in the heart of Ashland. The room we stayed in (Peter Beaumont) was very comfortable and elegantly furnished. The bed was huge. You had to climb up to get into it. The room had all the climate controls and lightings fictures expected of a modern hotel, but somehow integrated into a Victorian setting. Our breakfast was delicious, with great patries and cooked dishes. The only disappointing aspect of our stay was our checkin. The one person at reception was on the phone, and two staff members in the adjacent bar were far too busy chatting with each other to help out, even though their colleague on the phone was calling them for help.

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Thank you so much for joining us! We do strive to offer the best in both amenities and service. We have since had a slight change in staff and I am very sorry that your first impression was that one. I hope that you join us again soon, and that we can show you that is not the standard that we set. Thank you very much for taking the time to write us. Regards, Drew Gibbs

The Winchester is exceptional in every area--great rooms, superb service, perfect location for walking to plays, a beautiful garden & grounds, friendly ambiance, and a better-than-ever restaurant. Our favorite inn anywhere, not just in Ashland.

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Thank you for the kind words! I will be sure to pass them along to the staff as they take great pride in their work. We hope to see you again soon. Regards, Drew Gibbs

I stayed in the Catherine M. room, which is more modestly-priced than others. I was expecting far less than I received, in beauty, charm, size, and polish. And it was utterly spotless to the naked eye, a huge plus for me. Even the view, which faced the other building and the courtyard walkway, was darling...felt almost European. The biggest surprise was the quality of the restaurant, which I never expected to rival the Cowboy Bistro, but it easily (easily) did. There is genuine creativity coming out of the kitchen, with excellent preparation. My only fault is that I dined there on my way back through town, about a week later, and ordered two of the same items I had previously tried: they weren't quite as fresh, crisp, or spot-on as a week before (I don't think it was a case of too high expectations; literally, the greens on one dish were just on this side of wilted). However, the one new dish I tried was just as good as I'd hoped for. Service is charming all the way around. Free parking, just steps from OSF. The Winchester is a true Ashland gem.

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Thank you so much for joining us! The kitchen enormous pride in their efforts to offer delicious and exciting cuisine in a town as full of fantastic restaurants as Ashland is. I hope your next trips are as wonderful as the last. Regards, Drew Gibbs

The first room was WAY too small. The second room was great, but below the kitchen. Hence, way too much noise in the morning from people walking overhead. I bet there are better rooms and I'd be happy to stay again if we could be in a better room! Also, the food was good, but a little too gourmet for breakfast. To be honest, something a bit simpler would have been better.

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Thank you for staying with us! All the rooms are unique, and what we have found is that long time guests find their favorites. Not every room we offer is for every guest, that is some of our appeal. I am however very sorry that there was a noise issue with the second room. That is not something that comes along with a comfortable stay. We also are happy to cater to your preferences for dining. The kitchen is happy to make whatever you would like with enjoy notice. Thank you for taking the time to write us! Regards, Drew Gibbs

Our suite was extremely comfortable. We enjoyed our stay very much and would love to come return!!

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I am thrilled to hear that you enjoyed your stay! Hope to have you back soon! Regards, Drew Gibbs

We enjoyed our stay and look forward to another visit next year.

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Thank you so much for joining us! Regards, Drew Gibbs

We stayed two nights at the Winchester Inn in July. Was originally looking for something less expensive, but this turned out to be worth it. Location, grounds, ambiance, nice staff, good food & drink ... a charming stop on our trip. The Winchester is in a great location only a block off the main drive in Ashland. Based on the setting, beautiful grounds and relatively high room rate, this would be a great place to stay if you plan to actually spend time at/near the Inn. A little reading, sipping coffee or wine, spending time with someone ... this is a great spot. Running out early and coming back late, might as well find a less expensive place. Our ground floor room was nice with a comfortable seating area on the patio outside. We visited the wine bar one evening prior to heading out and enjoyed the ambiance as well as meeting some locals. The same wine bar offers coffee and newspapers in the morning, very relaxing to sip and read while looking out onto the gardens. The room comes with a breakfast credit. Our meal was fantastic. Only a couple minor recommendations. It would be great to have menus from some of the local dining establishments in the lobby (even though they have their own restaurant). The walkway area thru the middle of the inn could use some TLC. And a DVD player in the room would be nice for a R & R spot like this (it's 2011 ...). Those are extra touches I expect from a B & B.

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Thank you so much for joining us! We hope that you have a little more time next year to relax and as you said, enjoy what we have to offer. We are always striving to make improvements around the property. As you mentioned the walkway, we just had the wood floors refinished, and I am amazed that they look brand new. This is also the first year that we have started to put TVs in all the rooms. DVD players are the natural next step, but it is all in good time. We also do offer at the front desk, a large book of all the menus that we can find for local restaurants. We are always happy to get whatever you would like if you ask us, be it menus or reservations. I hope that you join us again soon so that you can see what improvements we've made. Thank you again for taking the time to write us! Regards, Drew Gibbs

We wanted to stay at one really nice luxurious place during our trip through Oregon and although Ashland is beautiful I could have spent my entire stay at this property.

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Thank you so much! Maybe next time you will just have to stay. Regards, Drew Gibbs

We had a lovely stay at the inn and enjoyed the delicious dinner on the porch and breakfast in the dining room. The room was very spacious, and our 4-year-old was comfortable and welcome at the inn. Love it that the location is only one block from the little main street shops. The garden, gazebo, and other outdoor seating were so pleasant for relaxing.

We stayed two nights at the Winchester Inn in Ashland. We tend to stay in a little less expensive places but found it hard to get a room during Shakespeare Festival season. But no complaints at all with our time at the Inn. Beautiful accommodations, beautiful gardens, friendly staff, great breakfast each morning. It is quite obvious the owners put the best into it, even down to the energy saving light bulbs peeking out of the old fashioned fixtures. Was definitely worth the extra money for the inviting, relaxing stay. It was lovely!

Ashland has many fine B&Bs, but Winchester is the superstar. Large, comfortable rooms; gracious amenities; fine dining (for dinner as well); and a friendly, hospitable staff. Absolutely no downside to the Winchester Inn.

We had another wonderful visit to Ashland and staying at the Winchester made it even better. Our room was not large, but it had two comfortable chairs. The grounds and the people could not have been nicer. The breakfasts are incredible and I think the Winchester Restaurant is the best in Ashland for dinner. We plan to stay there next year too.

Our expectations of the Winchester Inn has never let us down. From the time we step in the door we know that we will be served well. The hospitality and friendly smilling faces of all staff make us feel right at home. Rooms are alway emaculate and the wonderful breakfast that is served every morning makes you excited to wake up! Thank you for a wonderful relaxing escape!

Incredible service! Our dining experiences were sheer joy, and we're looking forward to coming back next year.

This is a beautiful inn with elegant amenities. We stayed in the patio room which had a small courtyard with a table and chairs. Enjoyed sitting out in the evening with a bottle of wine. The room was very tastefully furnished with nice furnishings and fantastic bedding. We stayed here many years ago and enjoyed it even more this time. The owners keep improving it. We will definitely plan on going back.

From the friendly and accommodating owners and staff, to the comfortable beds with soothing sheets, to the afternoon treats left in each room, to the flowers in the gardens, to the unique personality of each charming room, to the exquisitely delicious dining, The Winchester is not to be missed. Treat yourself.

Once again, my best friend and I had a wonderful weekend at the Winchester. Our room. the Queen Anne, was cozy and comfortable making it hard to leave in time for the theater. The breakfasts were so delicious and filling enough to take us through until dinner. We are looking forward to our next visit in 2012 already!

The weather was iffy but we got to sit in the garden for 5 o'clock whites. The young woman on the desk was cheerful and sweet, the fellow in the wine bar was condescending and unpleasant and not helpful about the wines. The breakfast was was amazingly good, the dinner fine.

[Resource Id: innkeeperresponse, Set: reviews]
Thank you so much for writing us! I am very sorry that you were not pleased with your experiences in the wine bar. I have spoken with our bartender and I want to assure you that this is not the sort of behavior that we expect of our employees. Again, I am sorry that your experience was less than exemplary. We will make every effort to make sure it does not happen to anyone else looking to join us.

We had a lovely time, however our room was directly underneath the winebar and we were kept awake well into the night with foot traffic overhead.

[Resource Id: innkeeperresponse, Set: reviews]
Thank you so much for letting us know! I am very sorry that your stay was not as you had imagined. I hope that while you were with us that you mentioned something to our staff as we are always trying to make your stay the most comfortable it can be. We are aware of the noise in the bar, and have taken steps to reduce and eliminate that noise (thicker mats and earlier hours). Again, I'm very sorry, and hope that you will return and enjoy the comfort that is due. Best regards, Drew Gibbs

The room was perfect in every way. The breakfasts presented creative dishes at an oft forgotten meal. Dinners were equally outstanding. Suggestions for activities, help with scheduling activities and help with finding very particular needs exceeded what I have learned to expect from concierge in the finest of urban hotels. The 2 block walk to the Shakespeare Festival is easy and pleasant. I can think of nothing negative to say.

Great location and very comfortable rooms. Breakfasts are wonderful and dinner delicious. Owners are very nice and accommodating. We have stayed here for almost 10 years and it never disappoints.

We've stayed several times and I always enjoy the Inn. I would have liked to have had a 'breakfast to go', as we were unable to stay until the breakfast room opened and yet we had paid for our meal! I've been to other B&Bs that gave us a paper sack meal to take on the road. P. Taylor, Portland, Oregon

[Resource Id: innkeeperresponse, Set: reviews]
I am so sorry to hear you had to leave without breakfast. It is always our policy to offer a full complimentary continental breakfast to go for our guests that have an early departure time and request the service. We do not charge our guests for breakfast. Instead, we offer it as an added bonus. If we were amiss in not providing this for you at your request, please accept our sincere apologies.

Our time at the Inn was very pleasant. Our room was very comfortable and the staff was very helpful and friendly.

We go to Ashland every year and always stay at the Winchester Inn. The accommodations are upscale and comfortable, the restaurant is excellent, and the people are cheerful and helpful. The inn is just two blocks from the theatres. What more could you want?

Suites are well-appointed with luxurious bedding and comfortable seating for reading and relaxation. Bathrooms are large with a great shower and our room had a 2-person jetted tub. Service was friendly, courteous and attentive.

We have gone to the Inn for almost 10 years. It has greatly enhanced our Shakespeare Festival Experience. The Inn improves every year. They are always making small tweaks. My only minor quibble in the past was the food at breakfast. Now, it is excellent and a highlight. Laurie Gibbs is a true host and knows how to make things right. I am usually somewhat critical but have nothing but positive feedback for Winchester Inn.

Always a pleasurable part of our venture south for the winter. Highly recommend this as a destination stop.

There were good and bad aspects of staying at the Winchester Inn. It is a beautiful property and well-maintained. The breakfast was good and the room was spacious and clean. The problem was that they do not warn guests that the rooms underneath the kitchen and restaurant are noisy. They have dinners and music on the weekends and of course breakfast in the morning. We were kept awake by dish carts loudly rolling over our ceiling and the footsteps of wait staff (earplugs were not adequate). The Inn offered to refund about 1/3 of the cost of our stay when I let them know that the noise had interfered with sleep but showed no inclination to inform potential guests about the noise issues with those rooms.

We stayed here the first night of our honeymoon and it was wonderful. They upgraded us to the courtyard suite and had a bottle of bubbly waiting for us on them. Our suite was so beautiful with a private entrance through the garden. Their was even a huge bathtub with jets and candles aligning the tub. The best part was the ridiculously soft robes and the incredibly soft sheets. They even sell them...they are that good. Our breakfast the next morning was delicious. Great presentation and flavor. I will need to come back to have dinner, the kitchen was closed when we were their. Would highly recommend. We walked to everything.

Romantic, great location downtown. Eleanor Rose suite was large, attractive and quite comfy.

We attended the 28th annual Dickens Christmas Feast, then spent the night in the Garden Room of the main house. The feast was incredible - very festive, great carolers between each course, and Santa at the end was impressive! The room was beautiful and very comfortable. The breakfast was very good too. We definitely plan to make this an annual event!

Michael and Laurie keep a beautiful property and provide a level of hospitality that is unequaled. There are lovely small touches in the graciously appointed rooms that allow for a sweet treat when one arrives, and all the necessaries to enjoy your own bottle of wine. The food at the Winchester in is wonderful.

Was just a one night stay to meet friends. Definitely would stay again if in the area.

The staff make you feel as though you are a visitor in their home - in fact, the whole place feels like visiting a friend. Great breakfasts and wonderful rooms. Absolutely one of our favorite lodgings anywhere.

This was our second stay with the good folks at Winchester Inn, we received the same great service and had a wonderful time. The rooms are gorgeous and unique, the hotel staff is friendly and attentive, & the food & service in the dining room is outstanding. Oh and be sure to talk to Andy in the Wine Bar! You might be able to find cheaper places to stay in Ashland, but you will find those other establishments lacking the value Winchester provides for your vacation dollar. Ted & Karen Fox Magalia, CA

My husband and I stayed here while visiting family in Medford over the Thanksgiving holiday. We decided to stay an extra night and the Inn was more than accomodating. The staff is very friendly and helpful. The Inn has a limited menu so what they serve is done to perfection instead of having dozens of items that are just OK. The morning before our last stay I asked if I could have the Chilaquiles and the server explained that the preparation took some time, but would be willing to put it on the menu for the following morning. Low and behold it was on the menu that morning. It was fantastic! This is by far the finest bed and breakfast I have ever had the pleasure to stay in.

Breakfast was exceptionally good and the dinner superb. Room was small, raised bed unnecessary and cumbersome; however the overall experience was excellent.

I decided to try a new place to stay in Ashland for my first trip there in the Fall. I was traveling solo without kids and husband so I really needed a place that was relaxing and took care of my every need. The Winchester Inn did just that. My first night was a bit rough only because my room was right below the Wine Bar. Since I was not seeing a play I was in bed fairly early so I heard all the noise of chairs being moved and the music. I mentioned the problem to Rebecca the next morning at breakfast and she arranged for me to move to a suite. So lovely, I got the best night sleep that I have had in a long time. I also had dietary requests that they always met. They knew who I was when I came for breakfast and for dinner and always accommodated my request for no wheat, cow's milk or refined sugar. Thank you to the entire staff for making my trip extra special. Thank you Andrew for the fabulous service at dinner and the wine recommendations. I had a very early flight and I had a wonderful continental breakfast waiting for me in my room the night before. Fresh fruit, cheese, ham and hard boiled eggs. I will definitely stay there again. I also loved being able to walk to everything, I usually stay at a b&b where we have to drive.

The Winchester Inn is a fabulous Bed and Breakfast! The room was ready before they said it would be. We checked into the Belvedere Suite and then left to have dinner with friends and see a play. When we come back next time, we will definately save the play for after breakfast the next day and just enjoy the room longer! We purchased a meat and cheese tray for after the play and it was perfect! The service was great and the room was amazing. I would highly recommend the Winchester Bed and Breakfast! We had a fantastic Anniversary weekend!

We've stayed at the Winchester Inn for years now at least twice a year when we attend the plays usually springtime and fall..It is the best place ever, the nicest people the winebar the food the beds, the bedding, everything you want is there..It is by far one of my favorite places and we travel alot. One of the stays we had a room that didn't suit us as there was a bit of noise from the street and they changed us immediately to a suite..Laurie, Michael and Drew are truly wonderful people and every detail is well thought out..We also love Andy in the winebar he is fun and very knowledgeable about wines. I forgot the other ladies name who is there and has been for years but she is wonderful too..You truly cannot be disappointed by a stay at this Inn!! Thank you all...We will be back. Helen Tanner and David Sybert Lake Tahoe CA

Central location, yet peaceful. Beautiful grounds. Our room was comfortable and roomy. I would stay at Winchester again.

We really enjoyed our stay at the Winchester. The service was fantastic (off to breakfast, when you come back, your room is made up). Friendly folks and gourmet food. Just blocks from the theaters. Overall, a great place to stay in Ashland.

[Resource Id: innkeeperresponse, Set: reviews]
I'm thrilled to hear that you enjoyed your stay with us. The staff always tries to make everything as comfortable and enjoyable as possible. We look forward to the next time.

The room and the Inn itself are without question beautiful and inviting. The breakfast was delicious. A few notes...if you are on a lower room of the main house (we were in the Enders room) you will hear every footstep from the wine bar and kitchen untill late at night and expect wake up noise at 5:00am as the staff is preparing for breakfast. It isn't slight, it's quite a bit of noise and makes sleep difficult. Also, the wall units are noisy and you can't turn them off so if your a light sleeper, take ear plugs. I felt that for the cost of the room there were a few details that could have made a better impression.

[Resource Id: innkeeperresponse, Set: reviews]
I'm very sorry to hear that there was an issue with the kitchen noise. We are working hard to find a solution to this problem. The kitchen staff has been addressed, and unfortunately they had arrived extra early in preparation for Easter Brunch. I hope you brought up the matter when you checked out as we are always welcoming feedback and do what we can. I hope that you would try us again.

As a family of four with two young children we thoroughly enjoyed our stay at The Winchester Inn. The accommodations, charming atmosphere, friendly staff and delicious food made this Thanksgiving one to remember. We would recommend this Inn to anyone!

We had a perfect evening! We loved the room with the fireplace, enjoyed the food and friendly faces, the privacy, and the peace and quiet...and the bed was so comfortable, with sheets so soft! We ended up using the fireplace for heat as we slept, as the Wall unit was noisy, but that made it more perfect in my mind!

We have stayed at the Winchester Inn before, years ago, and it is just as wonderful. The service, food, and accommodations were excellent. They are hard to beat; no complaints here!

Perfection! (and I'm not easy to please)

We've stayed many times over the years and always have the same great experience. Great food and very attentive staff.

We so enjoyed our stay in the Sylvan Room, with its charming windowseat overlooking a lovely garden. Delicious breakfast and attentive service topped off a great weekend.

The Winchester Inn is located just a couple of blocks from the Shakespeare Festival theaters and one block from shopping. The room was very nice, had a couch and chairs (no tv). There were three choices for breakfast: poached eggs, an omelet, or pancakes (French toast the second day), with different extras. Dinner was gourmet. Overall, a fantastic experience.

The Winchester Inn is a perfect place to stay in Ashland. The inn is one block from the Oregon Cabaret Theater and two blocks from the Oregon Shakespeare Festival. The inn has 18 rooms, individually and beautifully decorated. The beds are comfortable with fine linens and each bathroom fully appointed with big, fluffy towels! The meals here are wonderful! Breakfasts include a fruit and pastry plate followed by a delicious main breakfast entree. The dinners are fabulous, using fresh local produce. The inn has a full bar. The owners, Michael and Laurie Gibbs, along with son, Drew provide a comfortable and classy place to stay while in Ashland. It's a gem!

We just stayed here last night, the place was nice and private, but.. you hear the person above you!! We were in "brighton" a cute seperate place so we were thinking we wouldnt have any disturbances but we were kept awake from the people upstairs. The hot water ran out in about ten minutes so we had to rinse off really fast and turn it off... wait about 20 minutes and jump back in to finish washing where we had to leave off.. Having 3 small children with us made that really dissapointing. The food there is extremely fancy but not anything our kids even wanted to try, so the complementary breakfast was kinda a waist. They were very nice, and even came in while we were out and opened up the couch to a bed, and even made it for our son. They also knew we had an infant with us so they put a playpen in there along with a baby blanket.. that was so awesome. Overall it was good, but not a place I would go back to for that price.

[Resource Id: innkeeperresponse, Set: reviews]
Thank you for taking the time to write us a review. I'm sorry that your stay was less than satisfactory. I truly wish that something had been said while you were with us as we would have done everything we could to correct issues, such as examining our hot water heaters (which has since been adjusted) or making up special breakfasts for your children. Excuses don't change your experience but know that we are always striving to please our guests and hope that you would return for another visit. Sincerely, Drew Gibbs

everything is fabulous, including the food! (Great coffee!)

A wonderful place to stay and relax. Outstanding breakfast. Location is perfect for dining, shopping, and theater. Friendly, warm service.

The Winchester Inn gives the guest the complete B&B experience. The rooms are spacious and comfortable. The dining room offers excellent dinners and the wine bar offers an extensive wine list. The guest is made to feel welcome and valued.

Robert Gordon is a suite with a huge bed. inventive cooked breakfasts.

The room was beautiful and the service was amazing and it was a great experience!

Once we discovered the Winchester Inn in Ashland, we stopped looking for new places to stay. The owners staff are welcoming and cater to your every need without being overpowering. The rooms are beautifully appointed. Breakfast offers something for every appetite and the location is central to the theaters and park.

Ashland is wonderful and there is no better place to stay than at the Winchester Inn

Comfortable bed ever, elegant breakfast,charming innkeepers, amazing attention to detail, a wonderful Inn.

Outstanding property. Great staff and service

We've learned to expect the best accommodations and service and are never disappointed. From the first sight of the beautiful gardens and welcoming porch - cares slip away and we truly relax, knowing we will receive the best in all ways!

Wonderful Inn. Beautiful gardens, rooms, and great food.

We just love this place. This is our third time staying here and always the staff is helpful, the food delicious and the rooms oh so comfortable. We will be back next year!

[Resource Id: innkeeperresponse, Set: reviews]
Thank you so much for taking the time to share your experience of staying at The Winchester Inn. We are so pleased that you enjoyed your visit, and we look forward to seeing you next year!

One night at Winchester and tickets to one of the Shakespeare Plays were given to me and my husband as a Christmas present by my mother-in-law. I had a honeymoon like stay there!

Shakespeare Festival in Ashland five times a year.

This inn met my expectations.

Wonderful accomodations and ambience.

My husband and I stayed one night for our anniversary. I love to travel and try to stay in b&bs when I can: I have to say this property is outstanding. Attention to detail shows in every aspect, from the wonderful rooms (with great bathrooms!), to the neat wine bar where you can get a small snack before heading off to a play at the nearby OSF, to the gourmet breakfast the next morning. When they found out it was our anniversary, there was a bottle of chilled champagne awaiting us in our room (with truffles). When we checked in, the attendant gave us the keys to the unoccupied rooms so that we could check them out before committing to one. I understand that they serve some fantastic progressive dinners, as well, but we didn't dine there- reserve that well in advance, especially in summer. Overall, this is probably one of the top lodgings that I have ever stayed at. I can't wait to go again.