We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
All 37 Ashland B&Bs / inns

The Winchester Inn

35 South Second St., Ashland, OR 97520
Hotel website
Hotel amenities
Special Price
10% off room rate
Save Saved
You added The Winchester Inn to your Saves list
The Winchester Inn
Best prices for your stay
Enter dates for best prices
Check In Check Out
Show Prices
Compare best prices from top travel sites
Ranked #11 of 37 Ashland B&B and Inns
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 3 weeks ago
HazelHB Huntington Beach, California
  • Overview
  • Reviews (170)
  • Photos (32)
  • Similar Hotels
  • Amenities
  • Q&A
  • Room tips (31)
  • Location
  • More
Write a Review

170 people have reviewed this hotel

Traveler rating
See reviews for
Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (31)
Date | Rating
  • English first
  • Any
English first
Huntington Beach, California
Senior Contributor
29 reviews 29 reviews
8 hotel reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Wonderful location: near theaters, downtown and restaurants. Delicious breakfast and gourmet dinners at their Alchemy restaurant are prepared with best local ingredients. Fine wine bar, rooms are air-conditioned and free Wi-Fi!! Owners and staff make you feel welcomed

Was this review helpful? Yes
Portland, Oregon
17 reviews 17 reviews
9 hotel reviews
18 helpful votes 18 helpful votes
5 of 5 stars Reviewed July 22, 2014

My husband and I were very impressed with the Inn. We stayed for one night during the Shakespeare Festival and were sorry we were not staying longer. The Inn is in a great location and a very short walk to the theater and the shops. The property is absolutely beautiful. Great landscaping, gazebo, and seating areas that create a little... More

Was this review helpful? Yes 1
Mount Dora, Florida
1 review
4 helpful votes 4 helpful votes
2 of 5 stars Reviewed July 20, 2014

Let me say right away that, unfortunately, we were not able to visit the Inn for the two nights we reserved in July. My rating is based on our experience attempting to get at least a partial refund of our deposit after we were forced to postpone our trip to the northwest due to family issues. Be aware that if... More

Was this review helpful? Yes 4
Washington DC, District of Columbia
Top Contributor
139 reviews 139 reviews
31 hotel reviews
57 helpful votes 57 helpful votes
5 of 5 stars Reviewed July 16, 2014

The Winchester Inn is a lovely old collection of Victorian homes, gathered together on a hilly street up from the main street, with a superb restaurant, the Alchemy. The Inn is very well staffed, the rooms are finely appointed and staff goes out of its way to learn your name and room. The bar is a lot of fun and... More

Was this review helpful? Yes
Santa Barbara, Calif
Top Contributor
107 reviews 107 reviews
62 hotel reviews
65 helpful votes 65 helpful votes
5 of 5 stars Reviewed July 7, 2014

The Gibbs family really make one's stay here remarkable. We have been coming back for many years and will continue to do so. (We have booked for next year!) On this trip we had booked a room that was not our first choice, a function of booking a bit late. (There are a number of rooms, all a bit different).... More

Was this review helpful? Yes
Santa Cruz, California
2 reviews
5 of 5 stars Reviewed July 2, 2014

In June 2013 we went to Ashland's Oregon Shakespeare Festival for the first time and had dinner at the Alchemy Restaurant in the Winchester Inn on one of the evenings. We had a wonderful meal, enjoyed excellent service and liked the look of the inn very much. So, for our 2014 trip to Ashland at the end of June we... More

Was this review helpful? Yes
Portland, Oregon
2 reviews
5 of 5 stars Reviewed June 28, 2014

We stayed here on drive from Portland to Sacramento. I highly recommend this hotel and restaurant and bar. WiFi, parking, 2 blocks from Shakespeare. Fabulous dinner and bar. Breakfast was outstanding.

Was this review helpful? Yes
19 reviews 19 reviews
9 hotel reviews
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed June 10, 2014

We have been staying at the Winchester Inn for many years and always look forward to coming back for another visit. We are always welcomed by Michael, Laurie and now Drew to our comfortable and well-kept rooms. The inn is so close to the Shakespeare Fesitval theaters as well as the Oregon Cabaret Theater, we never need to move our... More

Was this review helpful? Yes
Ashland, Oregon
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 8, 2014

We are locals. We love the atmosphere, staff and food. Downside is portions are skimpy and there is only one veggie option for non-meat eaters. Coffee is excellent. Service is excellent. We go back in spite of the downside, but urge them to add more veggie options and double the potato portions.

Was this review helpful? Yes
18 reviews 18 reviews
13 hotel reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed May 27, 2014

This was our second trip to Ashland ( family member is in the OSF Company as an actor). We have done extensive research on B&B's and stayed last year at another site. We have also been to B&B's in many other cities. This was one of the nicest we've stayed in. Clean and comfortable rooms. Excellent breakfats. The gardens were... More

Was this review helpful? Yes 1
Owners: What's your side of the story?
If you own or manage The Winchester Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.
Manage your listing

Been to The Winchester Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about The Winchester Inn

Address: 35 South Second St., Ashland, OR 97520
Phone Number:
Location: United States > Oregon > Ashland
Price Range (Based on Average Rates): $$
Reservation Options:
TripAdvisor is proud to partner with Travelocity and Expedia so you can book your The Winchester Inn reservations with confidence. We help millions of travelers each month to find the perfect hotel for both vacation and business trips, always with the best discounts and special offers.

32 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (16)
Room/suite (7)
Hotel & grounds (7)
Bathroom (1)
Other (1)

Management photos: Courtesy of the property manager

All management photos (17)
Dining (1)
Room/suite (6)
Hotel & grounds (2)
Other (8)
Hotels you might also like...
Check In Check Out
Price Your Stay
Select tags to find the hotel that's right for you.
hotels in Ashland with
any amenities


Bar / Lounge Beverage Selection Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Restaurant Suites
Official Description (provided by the hotel)
The Winchester Inn offers luxury accommodations, affordable excellence, the restaurant features local ingredients with global inspiration, craft cocktails and boutique wines. We are the only Wine Spectator Award Winning restaurant in Ashland as well as the only restaurant with a Certified Sommelier on staff. Top Chef of 2012 - Pamela Lanier's B&B Guide. ... more   less 
Number of rooms

Questions & Answers

Questions? Get answers from The Winchester Inn staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?

See which rooms travelers prefer