The Winchester Inn

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

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.

Reviews

Overall
4.6

Write A Review
  • Guest room4.6
  • Service4.7
  • Value4.2
  • Cleanliness4.7
  • Onsite Dining4.7

A favorite disappoints

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.


Best breakfast ever

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!!!


Will definitely be back

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!)


Another wonderful stay at Winchester Inn.

5 on December 29, 2016

A wonderful place to stay in Ashland. Everything was spot on.


Winchester Inn

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.


Charming!

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.


Winchester Stay

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.


great weekend

4.6 on October 20, 2014

A great find in the center of Ashland. Staff could not have been nicer.


Winchester Inn--The Perfect Stay in Ashland

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.


Always a pleasure at Winchester Inn!

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.


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Rooms & Rates

Brighton

Brighton

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

Duet Suite

Duet Suite

  • Maximum Capacity: 5
  • Bathroom Private Bath
  • Beds 1 King , 1 Queen

Catharine M

Catharine M

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

Enders

Enders

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

Courtyard

Courtyard

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

Garden

Garden

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

Belvedere

Belvedere

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

Fordyce

Fordyce

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

Patio

Patio

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

Queen Anne

Queen Anne

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

Sylvan

Sylvan

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

Barbara Howard

Barbara Howard

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

Peter B

Peter B

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

Marjorie Roy

Marjorie Roy

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

Hargadine

Hargadine

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

Eastlake

Eastlake

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

Robert Gordon

Robert Gordon

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

Eleanor Rose

Eleanor Rose

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

Andrew G

Andrew G

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

Sunset

Sunset

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

Silverdale

Silverdale

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

Check Dates

Location

Location Type

Downtown, Mountains, Small town, Wine country

Airport

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

Directions to property:

Approx. 5 hours South from Portland, 6 hours North from San Francisco, 3 miles from I-5 East.

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, Hairdryer, Hot tub/whirlpool tub, Ironing Board, Radio, Satellite/Cable TV, TV, Telephone, Turndown Service, Wi-Fi, Wired internet

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

Policies

  • Check In:: 3:00 P.M.
  • Check Out:: 11:00 AM
  • Open All Year Round: Yes
  • Smoking Allowed: No
  • Drinking Allowed: Yes
  • Alcohol Provided Yes
  • Suitable For Children: Yes
  • Childcare Provided: Limited Babysitting services are available upon request.
  • Guest Pets Allowed: No
  • Disabled Access Limited

Terms and Conditions

  • Accepted payments AMEX, VISA, Discover, Mastercard, Personal checks, Travelers checks, Cash
  • 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

English

Resident Pets

Cats

About the innkeepers

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.

Check Dates

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.


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