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.
The latest reviews. The lowest prices. The perfect place to shop for hotels.

The Winchester Inn

Show Prices
Certificate of Excellence
Enter dates for lowest prices
powered by PriceFinder
Check In Check Out
1 room 2 adults 0 children
We check 200+ sites to find the latest and lowest prices.
Management photos
The Winchester Inn
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"]},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review

231 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
There are newer reviews for The Winchester Inn
See the most recent reviews
Showing 230: English reviews
Reviewed 25 August 2016

We had dinner at the WInchester Inn in Ashland, OR earlier this week and had a terrific experience. The Inn is a very pretty property and the dining room was spacious and very well appointed. The wine list is very good, including, of course, a large number of Oregon Pinots, but had French, Spanish and Italians wines as well. The...

 Report
Helpful?
Thank jeff s
Huntington Beach, California
Reviewed 17 August 2016

Convenient location for walking to Shakespeare Festival venues. Air conditioned, nicely decorated, superior quality bedding for a restful sleep. Refrigerator, coffee and Tea Forte in the room. Very helpful and friendly staff. Gourmet breakfast. Beautiful remodel and additions since we here last year: larger sitting area outside, bar for casual dining or late night snacks, huge suite with private entrance...

 Report
Helpful?
Thank HazelHB
Oklahoma City, Oklahoma
Reviewed 14 August 2016

Beautiful boutique hotel just off the main street(s) in Ashland. A series of stately old houses, beautifully restored. Large, very will appointed rooms with private deck for a glass of wine at the end of the evening. Only a few blocks to the theaters and park. We enjoyed our stay. It is quite expensive, but in August in Ashland, what...

 Report
Helpful?
Thank jwillner
Portland, OR
Reviewed 7 August 2016 via mobile

We have been coming to Ashland for the OSF for many years, and have stayed at many (most) of the lodgings in and around town - but not any more. For the last 8 years, our "home" has been at The Winchester Inn. Believe the reviews. From the warm welcome from the owners, to the gourmet breakfasts (included) to the...

 Report
Helpful?
Thank mdwpdx
Washington DC, District of Columbia
Reviewed 3 July 2016

The inn has grown with the addition of a bigger restaurant, remodeled gardens and a larger bar area. It's added a happy hour ($5 martinis and manhattans), and still offers guests a magnificent and calorific breakfast. Service is excellent and the baked goods offered in place of nightly chocolates are a good sweet touch. The owners continue to improve on...

 Report
Helpful?
Thank Lanxlad
Teaneck, New Jersey
Reviewed 28 June 2016

The room was spacious, the bed sheets luxurious, the breakfast (included) was delicious and very generously sized, the staff super accomodating. They picked up our theatre tickets though we were told that we would have to. Their assistance in giving suggestions for traveling, wine tasting and local sights demonstrated great knowledge and thoughtfulness. Kudos to the Winchester Inn.

 Report
Helpful?
Thank Eileen E
Jacksonville, Oregon
Reviewed 20 April 2016

...and enjoy a chilled white with your lovely meal. Historic building, pleasant ambiance, delicious food. Since I live nearby, I didn't stay here, but I definitely recommend it for drinks and dinner with friends.

 Report
Helpful?
Thank Annazonita
Eureka, California
Reviewed 1 April 2016 via mobile

Huge thank you to all of the owners & staff at The Winchester Inn & Alchemy for making our stay so special! Drew, Cate, Laurie and Dena provided us with such beautiful accommodations and the absolute best service. We even had the pleasure of chatting with their Bar Manager, Jen, who makes incredible cocktails! If you're staying in Ashland, you...

 Report
Helpful?
Thank chai892
Reviewed 15 January 2016

Honestly I have never written a review but my experience was dreadful! I came to Ashland to look at rentals as I planned to relocate. Upon arrival I found NO parking. But that was the least of it! I was confounded when I found the phone in my room did not work... matter fact none of them did. So as...

 Report
Helpful?
1Thank Pamela G
Tucson, Arizona
Reviewed 31 December 2015 via mobile

Our visit was perfect. The Winchester Inn is ideally located just steps from Main Street with shopping and restaurants. Our room was beautiful, comfortable and full of amenities. The gourmet breakfasts were huge and delicious. And the treats in the afternoon were such a nice touch. This was a great choice!

 Report
Helpful?
Thank billdenised86

75 photos of this hotel

Traveller photos: See what travellers like you saw

Viewed
All Traveller Photos (58)
Viewed
Dining (1)
Viewed
Hotel & Grounds (13)
Viewed
Room/Suite (16)
Viewed
Bathroom (1)
Viewed
Other (27)

Management photos: Courtesy of the property manager

Viewed
All Management Photos (17)
Viewed
Room/Suite (6)
Viewed
Dining (1)
Viewed
Hotel & Grounds (2)
Viewed
Other (8)
Check In Check Out
Hotels you might also like...
Travellers also viewed these Ashland hotels
0.1 km away
Ashland Springs Hotel
Ashland Springs Hotel
#6 of 19 in Ashland
644 reviews
4.1 km away
Ashland Hills Hotel & Suites
0.6 km away
Plaza Inn & Suites at Ashland Creek
Show Prices
Show Prices
Show Prices
0.6 km away
Best Western Bard's Inn
Best Western Bard's Inn
#3 of 19 in Ashland
737 reviews
0.4 km away
Stratford Inn
Stratford Inn
#5 of 19 in Ashland
534 reviews
4.2 km away
BEST WESTERN Windsor Inn
Show Prices
Show Prices
Show Prices

Amenities

Highlights
  • Free Parking
  • Restaurant
  • Breakfast included
  • Bar/Lounge
  • Free High Speed Internet ( WiFi )
About the property
  • Non-Smoking Hotel
Things to do
  • Restaurant
  • Bar/Lounge
Room types
  • Suites
  • Non-Smoking Rooms
  • Family Rooms
In your room
  • Air Conditioning
Internet
  • Free Internet
  • Free High Speed Internet ( WiFi )
Services
  • Free Parking
  • Breakfast included
  • Business Centre with Internet Access
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 

Additional Information about The Winchester Inn

Address: 35 S 2nd St, Ashland, OR 97520
Region: United States > Oregon > Ashland
Price Range: €115 - €360 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — The Winchester Inn 3.5*
Number of rooms: 20
Reservation Options:
TripAdvisor is proud to partner with Booking.com so you can book your The Winchester Inn reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
Is This Your TripAdvisor Listing?
Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.
Claim Your Listing

Questions & Answers

Here's what travellers have asked, with answers from The Winchester Inn staff and other travellers.
2 questions
Ask a question

See all questions (2)

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 travellers prefer

“The Duet Suite entrance had no stairs to climb which made it especially nice.”
 of 5 bubbles sarahsG3285OL, 28 Nov 2016 | Read review
“There are a few rooms in the carriage house, they are darker and not my first choice. Also there are only a few with King beds.”
 of 5 bubbles Beentheredonethat47, 27 Sep 2016 | Read review
“We did not stay at the inn--only ate dinner there.”
 of 5 bubbles T2466SHjeffs, 25 Aug 2016 | Read review
“Prefer convenience of room in the main house for breakfast. Detached rooms more private”
 of 5 bubbles HazelHB, 17 Aug 2016 | Read review
“We like the rooms at the front overlooking the garden or the street.”
 of 5 bubbles Lanxlad, 3 Jul 2016 | Read review
5 of 5