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 Winchester Inn

3.0 of 5
35 South Second St., Ashland, OR 97520
Hotel website
Hotel amenities
The Winchester Inn
Ranked #9 of 36 Ashland B&B and Inns
Show the lowest price for this hotel*
Enter dates 1 night 2 nights
Show Prices
* We search the top travel sites for the best price
Hotwire.com Agoda.com Priceline.com
and 3 more sites!
Traveller Reviews
Room Prices
Write a Review

135 reviews from our community

    Trip type
Traveller rating
    117
    14
    0
    1
    3
Date Rating
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed 11 May 2013

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.

Was this review helpful? Yes
Portland, OR
2 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed 14 March 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... More

Was this review helpful? Yes 1
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 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.... More

Klamath Falls, Oregon
2 reviews
5 of 5 stars Reviewed 14 March 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!!

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 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... More

Victoria
Top Contributor
119 reviews 119 reviews
62 hotel reviews
Reviews in 50 cities Reviews in 50 cities
106 helpful votes 106 helpful votes
5 of 5 stars Reviewed 8 March 2013

The Winchester Inn provides the perfect balance of historical ambience and modern comfort. Throw in a liberal dash of great service and voila - perfection! Comfortable beds with amazing linens Well maintain, spotless rooms Central location Simply Divine breakfasts Great Specials I could go on.... Thanks Winchester Inn - we'll be back!

Was this review helpful? Yes
See 2 more reviews by iGuy for Ashland
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

Thanks for the kind words! Everyone does their utmost in making sure that we strive for that level of perfection that you seemed to have found. I hope you get the chance to join us again soon! Regards, Drew Gibbs General Manager Certified Sommelier More

Portland, OR
Senior Reviewer
6 reviews 6 reviews
5 hotel reviews
Reviews in 6 cities Reviews in 6 cities
9 helpful votes 9 helpful votes
4 of 5 stars Reviewed 19 February 2013

The Winchester is TOTALLY great and only reason I am not giving it a 5 star review is because of misleading information on the website. I SWEAR I read the website more than twice and the Garden Room was listed on the website as having a bathtub, which it does not. I really wanted a bathtub. I really like baths... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

Thanks for joining us! Our bartender (we love him too) is Eoin (pronounced Owen). And, we'll work on that private room with one table and a coffee pot! However, in all seriousness, we do tend to have the bar available, which has the coffee bar set up, and if you are looking for a little extra privacy we would be... More

Portland, OR
Top Contributor
163 reviews 163 reviews
70 hotel reviews
Reviews in 91 cities Reviews in 91 cities
200 helpful votes 200 helpful votes
5 of 5 stars Reviewed 13 February 2013

We have stayed at the Winchester for years on trips to Phoenix and Palm Desert. Honestly? This was the best stay yet. We stayed in the Robert Gordon Suite in the right building of the property. Fresh flowers, ice, and muffins awaited out arrival. With gas fireplace, and front Living Room (where I write this), the stay was exceptional. But... More

Was this review helpful? Yes
See 2 more reviews by grapdad for Ashland
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

I agree that the beds are outstanding. I think that combined with our sheets they make a combination that is practically unbeatable. I hope that while this was your best stay yet that the next one trumps it. Thanks again for the kind words and hope that you can join us soon! Regards, Drew Gibbs General Manager Certified Sommelier More

Bowen Island, Canada
Contributor
12 reviews 12 reviews
5 hotel reviews
Reviews in 10 cities Reviews in 10 cities
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed 5 January 2013 via mobile

We have just returned home from spending the New Year in Ashland. We were last in Ashland in October and knew that we had to come back and spend a day to explore this beautiful and seemingly prosperous town. The Winchester Inn is a three (I think) building B&B with a total of about a dozen rooms - each from... More

Was this review helpful? Yes 1
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

Thank you for joining us for New Years! It is always a busy time and I'm thrilled to hear that you enjoyed it. Now that we've reopened the restaurant and bar I hope you have the chance to come and experience the face lift! Regards, Drew Gibbs General Manager Certified Sommelier More

Chicago, Illinois
2 reviews
5 of 5 stars Reviewed 4 January 2013

Every time I come to Ashland (I'm up to nearly ten visits over the past 7 to 10 years), I stay at the Winchester Inn. Here are a few of the reasons why: great location, amazing accomodations (it's hard not to feel pampered), the most comfortable beds and seets I've ever slept in, extraordinary breakfasts (who ever writis about breakfast?!),... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

It is always a pleasure to soak up everything Ashland has to offer. I'm thrilled to hear that we continue to be one of those pleasures. I hope you have a chance to join us again soon! Regards, Drew Gibbs General Manager Certified Sommelier More

Spokane, Washington, United States
1 review
5 of 5 stars Reviewed 17 December 2012

Each time I have stayed in the Winchester I notice something newly added to the richness of decor, but somehow done in the most comfortable ways. What has not changed is the incredible standard of service. From a warm welcome upon arrival, to every personal need addressed throughout the stay...its impossible to miss the superior and authentic hospitality offered by... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

I will pass along the kind words to the staff. They take great pride in being able to offer the kind of service that always excels expectations. We hope you have a chance to join us again soon! Regards, Drew Gibbs General Manager Certified Sommelier More

Washington DC
1 review
5 of 5 stars Reviewed 16 December 2012

This richly furnished inn is just a short walk from the theaters of the Oregon Shakespeare Festival and a few steps from the tasteful shops and boutiques of Ashland. The inn manages to maintain a feeling of friendly informality wrapped in an aire of dignified elegance. Each room is is individually named and decorated with guests' comfort and convenience a... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
23 March 2013

Thanks you so much for the kind words! It is always a pleasure to have you join us, and can't wait to have you back! Regards, Drew Gibbs General Manager Certified Sommelier More

 
 
The Winchester Inn
Enter dates 1 night 2 nights
 
The Village Suites at Ashland Hills
Great value on a similar hotel
Ashland, OR
4.5 of 5 stars 232 Reviews
Show Prices
Still looking for a hotel?
Travellers also viewed these Ashland hotels
The Village Suites at Ashland Hi... 4.5 of 5 stars 232 reviews Ashland Springs Hotel 4.5 of 5 stars 307 reviews Country Willows Bed and Breakfas... 5.0 of 5 stars 78 reviews Green Springs Inn 4.5 of 5 stars 65 reviews
Show Prices ABS:HotelCheckRates-d95891?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d225890?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d80957?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
Show Prices ABS:HotelCheckRates-d1103010?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed_Hero
View all 19 hotels in Ashland, ranked by popularity

Been to The Winchester Inn? Share your experiences!

Write a Review Add Photos Add Videos

Additional Information about The Winchester Inn

Address: 35 South Second St., Ashland, OR 97520
Phone Number:
Region: United States > Oregon > Ashland
Amenities:
Bar/Lounge Business Centre Free Breakfast Free High-Speed Internet Free Parking Restaurant Suites
Hotel Style:
Ranked #9 of 36 B&Bs / Inns in Ashland
Price Range: €€€
Hotel Class:3 star (3*)
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.Pamela Lanier's B&B Guide just announced us as Top Chef of 2012. ... more   less 
Reservation Options:
TripAdvisor is proud to partner with Hotwire, Agoda, Priceline, Venere, Hotels.com and Tingo 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.

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
The Winchester Inn
Show the lowest price for this hotel (from Hotwire.com, Agoda.com, Priceline.com, and 3 more)
Enter dates 1 night 2 nights
Show Prices