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.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.

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"},"divClasses":"prw_rup prw_ibex_photo_carousel","moduleList":["handlers"],"js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"}},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review

230 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
Showing 229: English reviews
Start your review of The Winchester Inn
 Click to rate
Grants Pass, Oregon
Reviewed 1 week ago

The Inn was constructed in the late 1800's and is a true gem. There are multiple room choices, including family suites. Our stay was very comfortable and enjoyable. The restaurant Alchemy is a part of the property and is truly a 5 star experience. If you like cocktails, the bar is equally impressive with drinks we had never heard of...

 Report
Helpful?
Thank CraigAnd
Seattle, Washington
Reviewed 6 January 2017

Upon checking in after a long day of traveling on the road, we went to relax in the room. All of the decorative pillows from the bed and floors were in a huge pile on the floor. There were no extra pillows in the room--only two on the bed, and trust me, they were not particularly supportive so two pillows...

 Report
Helpful?
Thank Sarah J
Boston
Reviewed 25 December 2016 via mobile

Exceptionally well maintained/decorated inn. Very helpful staff, got us some last minute OSF tickets. Great location maybe 5 mins from theatres; but, quiet at night. Slow wifi. Great breakfast. The different rooms/ suites are very different, so look at what's available.

 Report
Helpful?
Thank BostonRedSoxNation
Redding, California
Reviewed 28 November 2016

My husband and I stayed in the Duet Suite with my daughter, son-in-law and their 8 month old baby. We wanted to give them a real vacation with nice accommodations and this was the place! The Duet doesn't look like a whole lot on the outside, but the inside was wonderful. Spacious, comfortable, clean, well stocked, great walk-in showers, beautiful...

 Report
Helpful?
1Thank Sarah S
Reviewed 28 October 2016

Ashland is a unique little town. The Winchester Inn reflects some of Ashland's more charming qualities. Each room features it's own style and decor. We were surprised to find that our room was more spacious than expected. The gardens and surrounding areas are quite lovely. Located within walking distance of the theatre and downtown, there is no shortage of shops...

 Report
Helpful?
Thank Raquel G
Reviewed 27 September 2016

I grew up in the era (and I know they are still out there) of B&B's being these places with lace, antiques and the owners in your face all the time. Pleasantly the Winchester Inn is not any of that. It is truly a boutique hotel with pleasant rooms with space, TVs, modern fixtures, tons of towels and amazing gourmet...

 Report
Helpful?
Thank Beentheredonethat47
Ashland, Oregon
Reviewed 25 September 2016

We have a lot of friends and family come visit Ashland - a very popular tourist destination - and when we can't accommodate them all at once, we often suggest the Winchester. It's historic, and so rooms are small, but mostly lovely, and the location is very near to our home on the other side of Lithia Park. However, more...

 Report
Helpful?
1Thank Lisa K
Victoria, Canada
Reviewed 29 August 2016 via mobile

We stayed at the Winchester Inn and had a lovely room with a view. The room was spacious and beautifully appointed.The bathroom also had good space and a great shower. We had a deck the overlook the valley. Breakfast is included with the room. It is a delicious 2 course gourmet meal in a lovely bright dining room. Service was...

 Report
Helpful?
1Thank Kathy D
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

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
636 reviews
4.1 km away
Ashland Hills Hotel & Suites
0.6 km away
Best Western Bard's Inn
Best Western Bard's Inn
#3 of 19 in Ashland
722 reviews
Show Prices
Show Prices
Show Prices
0.6 km away
Plaza Inn & Suites at Ashland Creek
0.4 km away
Stratford Inn
Stratford Inn
#5 of 19 in Ashland
532 reviews
4.2 km away
BEST WESTERN Windsor Inn
Show Prices
Show Prices
Show Prices

Amenities

Highlights
  • Free Parking
  • Restaurant
  • Breakfast included
  • Free High Speed Internet ( WiFi )
  • Bar/Lounge
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 South Second St., Ashland, OR 97520
Region: United States > Oregon > Ashland
Price Range: $103 - $432 (Based on Average Rates for a Standard Room)
Hotel Class:3 star — The Winchester Inn 3*
Number of rooms: 20
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