The Winchester Inn offers affordable excellence with an attention to detail and comfort; while the restaurant and wine bar offer innovative cuisine, award wining wine lists, and attentive service in a warm cozy atmosphere. This traditional Victorian stately home is in perfect harmony with its surroundings, situated in the midst of an English country garden. As guests approach the main building pansies line the path that leads to the front entrance, the gardens are encompassed by a herbaceous border whilst colorful tulips are scattered throughout the grounds. The interior is no less stunning, the rooms are a tribute to comfort and subtlety, with soft, warm shades and opulent furniture. Dinner may be taken in the popular restaurant, whilst in the summer, food is served outdoors. Wherever guests dine, the sumptuous flavors and textures are of the highest standards. The new wine bar provides a nice tasting of local wineries and a special nightly wine flight. The quaint gazebo is a perfect site for small weddings and receptions. Sporting activities available nearby include fishing, golf, ballooning or skiing while the more artistic guest may wish to visit the Ashland Shakespeare Festival or the Britt Music Festival, information on which may be obtained from the inn. If you are unable to find rooms through BedandBreakfast, please check out our personal availability calendar or call us to double check.
3.8 on October 01, 2017
The room was nice and cozy as were all of the amenities. One day we had a threadbare towel which was a surprise. Otherwise all was great. The breakfast was delicious but mine was cold when it should have been hot. Service at times was off. Dinner was an overpriced and inedible portion of duck. That was a great surprise. The service was also poor for dinner.
4.2 on September 04, 2017
Great location. Convenient to the downtown area. Relaxing environment in spite of a very busy season weekend. The breakfast was incredible.. You won't find any better!!!
3.4 on April 12, 2017
Very nice, fine landscaping. Much as would be expected. In room coffee self service would be nice as one could gently begin one's day rather than need to pop up and face the world.
4.6 on January 05, 2017
We only stayed overnight, but wish we stayed longer. We stayed in Sunset Room - very comfortable for 2 of us. Breakfast was fresh and delish (although they did forget my GF request). We wish we made a reservation for the onsite restaurant as they were all booked up (gives us one more reason to go back there!)
5 on December 29, 2016
A wonderful place to stay in Ashland. Everything was spot on.
3.4 on January 06, 2016
We loved our stay in the Courtyard Suite. Cozy, warm and pleasant inside, especially during a a very blustery and cold night! Great food, live music, and shops nearby.
4.8 on July 04, 2015
A beautifully decorated b&b. Great location in Ashland for the Shakespeare festival. A great bar and restaurant also. Staff were very helpful. Loved staying here.
4.0 on June 02, 2015
The stay at the Winchester was lovely. My room was exceptionally large and comfortable with pleasant views of trees in bud from the cozy window seat. With a bar and dining room on location, it was wonderful to have all of my needs met in one charming location.
4.6 on October 20, 2014
A great find in the center of Ashland. Staff could not have been nicer.
5 on October 15, 2014
We try to stay at the Winchester each year when we return to Ashland for the Oregon Shakespeare Festival. It is so popular that one must book well in advance. The Sunset Room is a real bargain for the price, and it has a very nice balcony for viewing the city and a bed that requires a small two step assistance to get up into the bed. And the bed is luxurious--fit for a queen. The Winchester is so convenient to the theaters--it is only a few minutes comfortable walk, which is a real convenience after the evening outdoor performance. The rooms are comfortable and nicely appointed. Everything is spotless and well-maintained. The staff is so friendly and accommodating--appearing literally out of nowhere when one is hefting an oversize bag up or down the stairs to voluntarily do the heavy lifting for you. Breakfast comes with the room and it is an amazing morning treat. I cannot recall exactly what we had the last time, but it was scrumptous. Usually there is a fantastic fruit plate, scones, a very appealing egg dish, French Toast or Waffles. What a start to the day! Their dinners are equally as good, although we enjoy other restaurants in Ashland and ensure we get some variety. We cannot say enough good things about the Winchester. You must stay there to believe it.
The Brighton Suite is located on the ground floor of the Carriage House and has a private entrance. It features a bedroom with a queen-size bed and a separate living room, full-size sofa/bed, electric fireplace, TV and a CD player. The wet bar has a refrigerator and bar sink. The private bath has a luxurious multi-headed shower.
The Duet Suite is a spacious 900 square foot, two bedroom, two bath accommodation. The suite has one king size bed and one queen, each with private access to their own bathrooms. The sitting area also shares a small bar that has a fridge, microwave and coffee pot. A private deck out front allows you to enjoy the weather. All rooms are equipped with flat screen TVs and iPod docks. Sleeps up to 5. Fully handicap accessible.
The Catharine M. Room is located on the second floor of the Heritage House and has a queen-size bed. The private bath has a bathtub and shower. The small balcony, which is shared with the Andrew G. Room, has views of the garden walkway and fountain.
The Enders Room is located on the ground floor of the Main House and has its own private entrance. The room has a king-size bed and a twin-size bed and a private bath with tub and shower. The room also has two upholstered chairs and ottoman.
The Courtyard Suite is located on the ground floor of the Larkspur Cottage and has a private entrance from the gardens. It has a queen-size bed and a living area with a sofa, TV, and a CD player. The wet bar has a refrigerator and bar sink. The private bath has a two-person jetted tub, as well as a separate shower.
The Garden Room, located on the second floor of the Main House, has lovely views of the Inn’s tiered gardens from the cozy bay window seat. It has a queen-size bed and a private bath with a tiled walk-in shower. The sink is inside the top of an antique dresser in the room. Two comfortable wicker chairs and coffee table provide a nice sitting area.
The Belvedere Suite is located on the second floor of the Larkspur Cottage and has a private entrance. It has a beautiful bay window seat overlooking the gardens and gazebo. There is queen-size bed and a living area with a gas fireplace, TV, and a CD player. The wet bar has a refrigerator and bar sink. The private bath has a two-person jetted tub, as well as a separate shower.
The Fordyce Suite is located on the second floor of the Main House and has views overlooking the Inn’s tiered gardens. This truly elegant suite has a king-size bed and two luxurious Bergère chairs with ottoman. The suite includes a TV, CD player, gas fireplace and a wet bar with bar sink and refrigerator. The spacious travertine marble bathroom features a romantic two-person jetted tub as well as a separate shower.
The Patio Room is located on the ground floor of the Main House and has its own private entrance. The private secluded garden patio features a lovely wall fountain and has a table and two chairs. The room has a queen size bed, flat screen TV, wet bar with mini fridge as well as a beautifully tiled walk-in shower.
The Queen Anne Room, located on the second floor of the Main House, has views overlooking the central courtyard gardens. It has a queen-size bed and a twin-size bed. The private bath has a walk-in tile shower. Two wing-back chairs with ottomans provide a comfortable sitting area.
The Sylvan Room, located on the second floor of the Main House, is a bright room looking out over the stately Almond Tree from the bay window seat. It has a queen-size bed and a private bath with a walk-in tile shower. The sink is inside the top of an antique dresser in the room. The loveseat provides a sitting area and is also available as a fold-out twin bed.
The Barbara Howard Suite is located on the third floor of the Heritage House. It features a bedroom with a king-size bed and a separate intimate living room with gas fireplace, TV, a CD player and a refrigerator. The spacious private bathroom has a romantic two-person jetted tub as well as a two-person shower.
The Peter Benjamin Room is located on the ground floor of the Heritage House and has a private entrance. This spacious room has a king-size bed as well as a sitting area with a full-size sofa/bed and chair. The private bathroom has a bathtub and shower.
The Marjorie Roy Room is located on the second floor of the Heritage House. It has a queen size bed with large bathroom and comfortable sitting area. It also has a private balcony comfortable for two that looks over the Cascade Mountains.
Our finest suite with views of the surrounding hills. The spacious 1000 square foot suite has a fire place and wet bar in the living room with a private balcony. The bedroom features a king size bed with spacious accommodations, as well as a bubble tub and seperate shower in the bathroom.
The Eastlake Room is located on the ground floor of the Main House and has its own private entrance. The room has a king-size bed, a comfortable sitting area with wet bar and mini fridge as well as a private bath with a beautifully tiled walk-in shower.
The Robert Gordon Suite is located on the ground floor of the Heritage House and has its own private entrance through french doors that open out to the garden walkway. It has a king-size bed and a separate living room with a large desk, gas fireplace, TV, CD player and refrigerator. The bathroom has a one-person jetted tub with shower.
The Eleanor Rose Suite is located on the third floor of the Heritage House. This large room has vaulted ceilings, lots of windows, a king-size bed and two comfortable extra-wide chairs. There is a gas fireplace, TV, CD player and a refrigerator. The private bath has a two-person jetted tub with shower.
The Andrew G. Room is located on the second floor of the Heritage House and has a king-size bed and a full-size sofa/bed. The private bath has a bathtub and shower. The small balcony, which is shared with the Catharine M. Room, has views of the garden walkway and fountain.
The Sunset Room is located on the second floor of the Main House. This newly renovated and enlarged room offers a king size bed, gas fireplace, and cozy sitting area. In addition, it features a private balcony with views of Ashland's surrounding hills. The bathroom includes a walk-in shower.
The Silverdale Suite is located on the second floor of the Carriage House and has a private entrance. It features a bedroom with a queen-size bed as well as a seperate living room with sofa, electric fireplace, TV, and a CD player. The wet bar has a refrigerator and bar sink. The private bath has a one-person soaking tub as well as a separate shower.
Downtown, Mountains, Small town, Wine country
Medford, OR (MFR-Medford-Jackson County) 20 miles
Approx. 5 hours South from Portland, 6 hours North from San Francisco, 3 miles from I-5 East.
Antique Shopping, Art Galleries, Concert venue, Gourmet/Fine Dining, Historical interests, Lake, Live Music, Movie Theater, Museum, National/State parks, Nature area, Rogue Creamery, Oregon Shakespeare Festival, 50+ Local Wineries, Performing Theater, Picnic area, Religious Services, River, Ski area, Vineyard, Winery
Other, Country Inn, Urban Inn
Copier, Fax Machine, Fireplace, Internet Service, Private entrance, Wedding Facilities , Imported 600 thread count sheets, Certified Sommelier on Staff
Air conditioning, Alarm clock, Amenities Basket, Bath robes, CD player, Coffee/Tea facilities, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Radio, Satellite/Cable TV, TV, Telephone, Turndown Service, Wi-Fi, Wired internet
Bicycle riding trails, Cross-country ski trails, Downhill Skiing, Golfing, Hiking trails, Kayaking, Mountain Bike trails, Annual Dickens' Feast, Shopping, Ski rentals, Whitewater Rafting
Michael & Laurie Gibbs
The best part of running a B&B is getting to know all the return guests. It is like have an extended family that comes to visit every year.
Gourmet two course breakfast
Low fat , Restrictive , Vegetarian Gluten Free, Please inquire.
Sous Vide Filet Mignon
Filet Mignon cooked sous vide with a Rogue Creamery Bleu Cheese and caramelized shallots compound butter and a sauce perigueux.