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The Winchester Inn

35 South Second Street , Ashland, OR 97520 USA (Show map)
4.6
251 Reviews
$90 - $405
per night

Check Dates

About

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.

Rooms & Rates

Garden Room

The Garden Room (located on the second floor of the Main House) with its beautiful bay window overlooking the tiered gardens, has a queen size bed and a private bath with an antique claw foot tub. Soft blue greens and white highlight this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Sylvan Room

The Sylvan Room with its large bay window and pillow filled window seat, look over a 60 year old alomond tree. decorated in muted shades of soft green and beige.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Queen Anne Room

The Queen Anne Room, luxurious with a both feather bedded queen bed and twin and a half canopy over the queen. This room boasts a suite of antique furniture that sets the soft tones of yellow and green to a picture perfect finish The private bath includes an antique claw foot tub.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen , 1 Twin

$140$205

Fordyce Suite

The Fordyce Suite is our newest renovation, located in the Main House on the second floor overlooking the garden and gazebo. The suite has a two person jetted tub, in a luxurious bathroom of travertine marble. The suite also features a king size bed, feather bed, a fireplace, TV, stereo and wet bar.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 King

Nightly Rate: $190-$299

Sunset Room

The Sunset Room has a queen size bed with feather bed and a private bath with a shower. French doors open onto a balcony where our guests enjoy the beautiful sunset over the hills of Ashland. This room is restful in shades of blue and salmon.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $140-$195

Patio Room

The Patio Room has a queen size bed with feather bed, private bath with antique claw foot tub. The private entrance opens upon a semi-secluded patio with a fountain. This room is fresh in florals and shades of, green, and peach.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Eastlake Room

The Eastlake Room, has a queen size bed, with feather bed private bath and antique claw foot tub. Enjoy a private entrance from the garden walkway. This room is decorated in shades of taupe with burgundy and cream toile with forest greens.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Enders Room

The Enders Room is spacious and has two beds, a king and a twin both topped with feather beds. The private bath has a conventional tub and shower. There is a convenient entrance from the garden path. This room is appointed in neutrals and sage green tones.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King , 1 Twin

$140$205

Robert Gordon Suite

The Robert Gordon is a deluxe suite featuring a spacious sitting room, with a fireplace, tv stereo, honor bar which adjoins the bedroom with a king size bed topped with a feather bed, private bath with a one-person jetted tub. Florals and shades of burgundy, cream, and pinks decorate the room. French doors open out to a garden walkway. Wheelchair accessible.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

$190$299

Peter Benjamin Room

The Peter Benjamin Room with its king size bed topped with a feather bed. Private bath A large room with a sitting area, offering a sofa that opens to a full bed. Outside the room is a large deck with fountain and gardens This room is decorated in florals and shades of green and beige.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 King

$140$205

Marjorie Roy Room

The Marjorie Roy has a queen size bed with feather bed. A beautiful bay window allows for sunshine and a pleasant view. There is also a small balcony for our guests to enjoy. The room is trimmed in shades of green, white, and burgundy and a rollaway is possible, but a snug fit in this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Catharine M. Room

The Catharine M. has a queen size bedwith feather bed. Private bath. The balcony is shared with the Andrew G.which is next door. This room is decorated in beige and pinks.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Andrew G.

The Andrew G. (located in The Heritage House) has a queen size bedwith feather bed as well as a sofa hide-a-bed. This room is finished in florals and shades of green and white. A small balcony is shared with the Catharine M.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 Queen

$140$205

Eleanor Rose Suite

The Eleanor Rose Suite is a spacious suite with high vaulted ceiling, king size bed with feather bed. A fireplace with TV stereo and honor bar and coffee maker ar a part of this suite. A private bath with a jetted tub for two plus shower. This room is lovely in shades of beige, cream, and accents of blue, and can accommodate a rollaway.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

$190$299

Barbara Howard Suite

The Barbara Howard Suite is located at the front of the building. It has a king size bed with feather bed a two person shower and two-person jetted tub. This suite has an intimate sitting area with a fireplace, TV stereo, honor bar, coffee maker and window seat. The room is charmingly appointed in florals and shades of beige and green. A rollaway is possible, but it is snug.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 King

$190$299

Courtyard Suite

Set into the tiered gardens the Courtyard Suite offers a queen size bed with feather bed as well as a sofa hide-a-bed. Wet bar , coffee maker, TV and stereo The bath has a large two person jetted tub and seperate shower. The Courtyard has a stunning view of the gardens and gazebo and French doors open to a lovely garden walkway. Burgundy, white, and green bring the gardens into this room.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

$190$299

Belvedere Suite

The Belvedere Suite is located on the second floor of the Larkspur Cottage has a queen size bed with feather bed and fireplace, wet bar with honor bar, coffee maker, TV and stereo. A beautiful bay window seat overlooks the gardens and gazebo with lovely views of the valley. This suite is light and airy revealing the floral prints and shades of green, white, and pastels to their best advantage. A rollaway is possible in this room.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

$190$299

Brighton Suite

The Brighton Suite is located in The Carriage House, this two room suite offers a seperate living room with sofa bed,fireplace and wet bar, TV and stereo. The bedroom has a queen bed with feather bed. A private bath offers a spa shower.

  • Maximum Capacity: 4
  • Bathroom Private Bath
  • Beds 1 Queen

$190$299

Silverdale Suite

Silverdale Suite, with its high vaulted ceilings and hard wood floors, offers a full living room,fireplace, wet bar, tv and stereo A queen size bed topped with a feather bed in the bedroom. Private bath with soaking tub and large walk-in shower. Shades of burgundy and green accent this suite.

  • Maximum Capacity: 3
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $190-$299

Guest Rooms

Guest rooms offer at least a queen size bed with private bath. Full two course gourmet breakfast is included with your stay.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $140-$195

Suites

Suites are larger than guest rooms with queen or king size beds. Some suites have jacuzzi tubs and fire places. All suites come with TVs and include a two course gourmet breakfast in the morning.

  • Maximum Capacity: 2
  • Bathroom Private Bath
  • Beds 1 Queen

Nightly Rate: $190-$295

Check Dates Visit Website

Reviews

Overall
4.6

Write A Review

  • Guest room4.6
  • Service4.7
  • Value4.2
  • Cleanliness4.7
  • Dining4.7

Score Breakdown based on
251 Reviews

Write A Review

Ashland's Best Lodging!

4.8 on August 22, 2014

Beautiful, distinctive rooms in an ideal location--a short walk to theaters. The restaurant, Alchemy, is among the best in town. Beautiful gardens, friendly staff, nice amenities in suites.


Simply the Best

5 on August 18, 2014

The Winchester does everything right. Amazing attention to detail, providing comfort with warmth and charm. Its proximity to the Oregon Shakespeare Festival is an added bonus (3 minute walk). The Winchester is one of those places that charges a full price but feels like a bargain because it is perfect. We can't wait to go back.


Lovely Interlude in Busy Lives

4.8 on August 13, 2014

Delicious sheets and Robert the cat. Also wonderful breakfasts and close to OSF. It's spendy, but everything in Ashland is and the Winchester was worth the money. We will return next year.


Winchester Inn -Great Bed and Breakfast;

4.8 on August 03, 2014

Wonderful room & formal breakfast; great location, easy walk to the Oregon Shakespeare Festival and Downtown. Terrific Restaurant but a bit pricey. We will go back, hopefully soon.


just getting better and better!

4.8 on July 30, 2014

just getting better and better over the years. food, service, friendliness all top notch. the gardens and gazebo were lovely hang out spots. cant wait to go again for our next Oregon Shakespearean Festival visit


Absolutely Outstanding

5 on July 16, 2014

The Winchester Inn was my first B&B experience and I'm very glad it was. Our stay was amazing. The property is beautiful and located near all the major attractions in Ashland. We stayed in the Courthouse room and it was beautifully prepared for our arrival. All the staff were friendly and courteous. I hope that all my future B&B stays go as smoothly as our stay at The Winchester Inn.


Sunset Room is Small, Couldn't Control Heat

3.2 on July 09, 2014

The Winchester Inn is quite lovely and has a great location. We were in the Sunset Room which turned out to be quite small once the suitcases were there. We had drinks and a complimentary appetizer and dessert at the bar. The food and drinks were great and the service was friendly and informative. My only problem was that we were unable to control the room temperature. The thermostat did not seem to respond. I went to the front desk for help, but in the evening there was no one there who was knowledgeable about how to get the heat to work. Otherwise, it was a pleasant stay.


Birthday Weekend

5 on July 07, 2014

We stayed at the Winchester Inn for my husband's birthday. The staff was so friendly, the rooms, neat and clean and the food was fabulous. The waitress even put a happy birthday note on his breakfast plate. We have stayed here several times and always love it.


Wonderful inn

4.2 on June 30, 2014

The inn is very well run: gracious service and excellent food. The rooms are spotless and well appointed. The location cannot be beat: you are no more than 2 blocks from anything you might want to do in Ashland. The only down side is that some of the rooms are dark. If this doesn't matter to you, then it's perfect. Enjoy!


Comfortable stay in Ashland

4.2 on June 28, 2014

The rooms are very comfortable. We stayed upstairs in the main house and had a balcony with a view over the mountains. The garden is a quiet, pleasant place to sit. The location is within easy walking distance of the Shakespeare Festival, the park and many restaurants. The restaurant at the inn is excellent with a pleasant bar and wonderful food and service. Altogether a very enjoyable place to stay in Ashland.


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Location

Location Type

Downtown, Mountains, Small town, Wine country

Airport

Medford, OR (MFR-Medford-Jackson County) 20 miles

Area Attractions

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

Inn Details

Establishment type

Other, Country Inn, Urban Inn

On-site amenities

Copier, Fax Machine, Fireplace, Internet Service, Private entrance, Wedding Facilities , Imported 600 thread count sheets, Certified Sommelier on Staff

Room amenities

Air conditioning, Alarm clock, Amenities Basket, Bath robes, CD player, Coffee/Tea facilities, In-room internet, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Radio, Satellite/Cable TV, TV, Telephone, Turndown Service, Wi-Fi

On-site activities

Bicycle riding trails, Cross-country ski trails, Downhill Skiing, Golfing, Hiking trails, Kayaking, Mountain Bike trails, Annual Dickens' Feast, Shopping, Ski rentals, Whitewater Rafting

Check Dates Visit Website

Policies

  • Check In:: 3:00 P.M.
  • Check Out:: 11:00 AM
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Suitable For Children: Yes
  • Guest Pets Allowed: No

Terms and Conditions

  • Deposit Amount Required: One nights pre payment is required for each reservation booked.
  • Cancellations: Please check upon reservation.

Innkeepers

Name(s)

Michael & Laurie Gibbs

Languages spoken

Some German, English

Resident Pets

None

Check Dates Visit Website

Meals

Breakfast

Gourmet two course breakfast

  • Time Served: 8:00-9:30 A.M.
  • Serving Location: Dining Room, Guest room

Special meal options

Low fat , Restrictive , Vegetarian , Gluten Free, Please inquire.


Signature Dish

Sous Vide Filet Mignon
Filet Mignon cooked sous vide with a Rogue Creamery Bleu Cheese and caramelized shallots compound butter and a sauce perigueux.


Recipes

Details

BedandBreakfast.com Diamond Collection

35 South Second Street , Ashland, OR 97520 USA (Show map)

Property highlights


Free $100 gift card with a $350+ purchase
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