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!!!
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.
4.8 on October 14, 2014
The Winchester has become our home away from home when in Ashland for the Oregon Shakespeare Festival -- or for any other reason. We love it, and look forward as always to our next visit.
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.