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.

“Best place to stay in Ashland”
Review of The Winchester Inn

Best prices for -
Check In mm/dd/yyyy Check Out mm/dd/yyyy
Prices are for 1 room, 2 adults
Show Prices
Compare best prices from top travel sites
and 5 more sites!
The Winchester Inn
Ranked #9 of 31 Ashland B&B and Inns
Certificate of Excellence
Reviewed July 8, 2013

We have stayed here many times over the last 10years. True , warm hospitality, delicious breakfasts, great wine selections and welcoming bar, Lovely, comfortable rooms, well kept, charming gardens. Walking distance to theater. The owners really care.

  • Stayed: July 2013, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
2  Thank mark h
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review
Reviews (239)
There are newer reviews for The Winchester Inn
See the most recent reviews
Traveler rating
Traveler type
Time of year
Language

102 - 108 of 239 reviews

Reviewed June 24, 2013

We stayed in the Fordyce room. Top notch. We requested wine and truffles, and they were waiting for us upon our arrival. We also ate in their dining room,now called Alchemy. The dinner was excellent. The staff was aware of our plans to attend a play, and they made the dining experience very delightful. The chef is quite talented. It is a superb menu, we felt like we were eating in a 5 star restaurant. Breakfast was also amazing. This is a great B & B.

Room Tip: Ask the managers for the best rooms. They won't steer you wrong!
  • Stayed: June 2013, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
1  Thank Katrina M
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 27, 2013

This is a high quality inn. We had the Sylvan Room and the Garden Room, both on the second floor. They were very nicely furnished, very well maintained, and quiet. I believe that all the bathrooms in the Inn were remodeled recently, and they are quite nice (our sinks were in the bedroom to make more room for the new shower and toilet).

The restaurant also seems to have been remodeled recently and looks very upscale. Breakfast was among the best that I have had at a B&B, and service was also excellent.

The owners are actively involved in running the inn, whether working at the front desk or serving in the restaurant, which is always a big plus.

One small complaint is that the rooms were pretty chilly by morning, no doubt due to thin insulation common in buildings of this age. But the modern wall heater/AC warmed up the room quickly in the morning (but was too noisy to leave on all night). Also, the window shades were not operable on all the windows.

Room Tip: Rooms on the second floor are quieter. If you need a quiet room, be sure to ask about that when you...
  • Stayed: May 2013, traveled with family
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
1  Thank InsideScooper
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 18, 2013

Excellent overall. The staff and room were incredibly beautfiul! However, I felt that my stay could've been greatly enhanced by the addition of cookies in the afternoon. At a previous B & B, the cookies they served were not only delicious, but made me feel at home.

  • Stayed: April 2013, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
1  Thank 901Anonymous
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed May 11, 2013 via mobile

My wife and I have stayed at the Winchester Inn at least a dozen times as we come yearly to the Shakespeare Festival. It never disappoints. The rooms are wonderful and deferred maintenance is unheard of. Proximity to the festival theaters could hardly be better and the food is great. It's a keeper that gets better each year.

  • Stayed: May 2013
    • Value
    • Location
    • Rooms
    • Cleanliness
    • Service
1  Thank AngusDad
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed March 14, 2013

The Winchester Inn is set on a steep hill one block from downtown Ashland. Steep flight of steps to the entrance and very steep, long flight of steps to the second floor where many of the rooms are located. Our room was tiny, dominated by a high bed that required a step-stool (provided), to climb into. All in all not recommended for seniors. On the plus side, the theater is justifiably famous, the town is very pleasant and it was a dynamite breakfast

Stayed: December 2012, traveled as a couple
3  Thank Pamela L
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this reviewResponded March 23, 2013

I am thrilled to hear that you loved your breakfast! However, I am terribly sorry that you had troubles with the property. While it is true that we do sit on a hill, we do have many older clientele join us every year. We are happy to help facilitate in anyway possible, such as getting you a ground floor room. While there is nothing we can do about the grade of the sidewalk, if mobility is an issue we can arrange to have your breakfast delivered to your room. I hope you know that the staff, when notified, will make every effort to make your stay more comfortable for you. If you have any questions or concerns please feel free to call me. I hope that you have the chance to join us again and try things anew.

Regards,

Drew Gibbs
General Manager
Certified Sommelier

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Reviewed March 14, 2013

Spent a magical weekend at the Winchester Inn during their annual Dickens Feast. Their beautiful, highest quality guest rooms to the fabulous meals was just heaven. Then add the lovely Christmas decorations, and the live vocal entertainment what a wonderful way to start the holiday season. We will be back again next year!!

  • Stayed: December 2012, traveled with friends
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
1  Thank jean19811
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this reviewResponded March 23, 2013

This last year marked the 30th annual Dickens' Feast, and I have to agree that it was a special one. I'm so glad to hear that you enjoyed your meal, as our Chef Billy, has been working hard to find that magical balance between new and familiar. Thanks for the kind words, and we are already hard at work for the next one!

Regards,

Drew Gibbs
General Manager
Certified Sommelier

Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Hotels you might also like...
Travelers also viewed these Ashland hotels
0.4 mi away
Plaza Inn & Suites at Ashland Creek
0.1 mi away
Ashland Springs Hotel
Ashland Springs Hotel
#5 of 19 in Ashland
685 reviews
0.3 mi away
Stratford Inn
Stratford Inn
#4 of 19 in Ashland
625 reviews
Show Prices
Show Prices
Show Prices
2.6 mi away
Ashland Hills Hotel & Suites
0.4 mi away
Best Western Bard's Inn
Best Western Bard's Inn
#3 of 19 in Ashland
826 reviews
2.6 mi away
Best Western Windsor Inn
Show Prices
Show Prices
Show Prices

Been to The Winchester Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about The Winchester Inn

Address: 35 S 2nd St, Ashland, OR 97520
Phone Number:
Location: United States > Oregon > Ashland
Amenities:
Bar / Lounge Beverage Selection Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Restaurant Suites
Hotel Style:
Ranked #9 of 31 B&Bs / Inns in Ashland
Price Range: $219 - $398 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — The Winchester Inn 3.5*
Number of rooms: 20
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 
Reservation Options:
TripAdvisor is proud to partner with Travelocity, Orbitz, Expedia, Priceline, Hotels.com, Hotwire and Agoda 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.

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