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 40 Ashland B&Bs / inns »

The Winchester Inn

3.0 of 5
35 South Second St., Ashland, OR 97520
Hotel website
Hotel amenities
Announcement
Best Chef 2012
The Winchester Inn
Professional photos
18 traveller photos
Ranked #6 of 40 Ashland B&B and Inns
4.5 of 5 stars 107 Reviews
Show the lowest price for this hotel*
Show Prices
*from our partners
Write a Review

107 reviews from our community

    Trip type
Traveller rating
    94
    10
    0
    0
    3
Date Rating
San Jose, California
Senior Reviewer
7 reviews 7 reviews
Reviews in 6 cities Reviews in 6 cities
2 helpful votes 2 helpful votes
“Top experience: hard to imagine any way to improve this place”
5 of 5 stars Reviewed 19 May 2012 via mobile

We spent four nights here. The breakfasts are fantastic, with excellent service. The location is excellent: short walk to the Shakespeare Festival, Lithia Park and many restaurants. Although the inn is just one-half block off the main commercial street, and our room sided to the back of commercial uses, it was extremely quiet. I don't think it is possible to... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
25 May 2012

Hello again! It was great to have you and your family join us! We are always thrilled to hear that you enjoyed your stay, and that the relative quiet of 2nd St. was just what you needed. The location is one that balances being just far enough from Main St to not have to fight noise pollution, but still just... More

San Francisco, California
Senior Reviewer
10 reviews 10 reviews
Reviews in 10 cities Reviews in 10 cities
12 helpful votes 12 helpful votes
“So much more than clean, well located and comfortable.”
5 of 5 stars Reviewed 17 May 2012

The Winchester is not a typical inn, in my experience. The comfort and amenities offered are more in line with a luxury hotel. We have stayed there three times now, each in connection with attending the Oregon Shakespeare Festival. The inn is a short walk to the Festival theaters, the main shopping street and lovely Lithia Park. Our room of... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
25 May 2012

Thank you for the kind words! It was great having you join us again! It is very true that we are not the typical Inn. With the restaurant and bar, as well as the other amenities we offer, the Winchester falls more in line with a boutique hotel than a Bed and Breakfast or Inn. All the rooms vary in... More

Wilmington, Delaware
Reviewer
5 reviews 5 reviews
Reviews in 2 cities Reviews in 2 cities
“By far the best place we've stayed in Ashland”
5 of 5 stars Reviewed 13 May 2012

We had a two night stay in the Sylvan Room. It had plenty of space, a very comfortable bed, a lovely modern shower with two heads and an east-facing window seat that got a lot of use. The food at the restaurant was great, with an awesome breakfast included that (for us) obviated the need for lunch! (We also had... More

Was this review helpful? Yes
See 3 more reviews by summanulla for Ashland
WinchesterInn, General Manager at The Winchester Inn, responded to this review
25 May 2012

It was a pleasure having you with us! It is wonderful to hear that you enjoyed the Sylvan room, especially the bathroom, as that room, along with five others, received bathroom and cosmetic renovations. The kitchen crew takes great pride in knowing that they put out some of the finest breakfasts and dinners. They staff also appreciate the compliments greatly.... More

Santa Rosa, California
Contributor
20 reviews 20 reviews
Reviews in 10 cities Reviews in 10 cities
7 helpful votes 7 helpful votes
“Great location & value”
5 of 5 stars Reviewed 29 April 2012

We have stayed here several times. Very comfortable. Nice bar. Great dinner and breakfast. Only regret is the 30 day cancellation policy. Only 2 blooks to Oregon Shakespeare Festival Theatres. Not just The Bard. Go for the modern plays, too. Not a bad seat at the indoor theatres, so not essential to spring for A+ seats.

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
25 May 2012

Thank you very much for taking the time to write us! It is always fantastic to hear that you enjoyed another stay with us! The insight for the Shakespeare Festival is especially helpful as not everyone realizes that there is a fantastic mixture of classic Shakespearean plays along with more contemporary shows mixed in, thus giving something for everyone. I'm... More

San Francisco
Reviewer
4 reviews 4 reviews
1 helpful vote 1 helpful vote
“Wonderful place to stay in Ashland”
5 of 5 stars Reviewed 13 April 2012

This is a delightful Inn only two blocks from the Shakespeare Festival. My room was lovely with fresh cookies every day. Free WiFi and HDTV in every room. And the breakfasts - Wow! Excellent dining and beautiful gardens. The staff could not have been nicer.

Was this review helpful? Yes
See 3 more reviews by Alison M for Ashland
WinchesterInn, General Manager at The Winchester Inn, responded to this review
26 April 2012

Thanks so much for taking the time to write us a review! We are always trying to improve on what we have here. And as such, I'm so happy to hear that you enjoyed your stay. Hope to see you again soon. Regards, Drew Gibbs General Manager Certified Sommelier More

San fransico
2 reviews
Reviews in 2 cities Reviews in 2 cities
“Beware....”
1 of 5 stars Reviewed 11 April 2012

We stayed at The Winchester last year, and a very expensive item was taken from our room. After a through search made of the room and luggage ( which i did) WITH the manager by my side, they did NOTHING!!!, not even a apology.This place was NOT worth the loss. We did not feel "pampered" with their lack empathy and... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
14 April 2012

I am so sorry you felt that you have been mistreated. As far as we can tell an item did go missing from the room, but myself, Drew Gibbs, the GM, and our desk manager, Rebecca Doran, and our head housekeeper, Kate Harter, looked through the room. Our housekeeping staff offered their belongings for search, and our head housekeeper, Kate... More

Bandon, Oregon, United States
Senior Reviewer
6 reviews 6 reviews
Reviews in 3 cities Reviews in 3 cities
4 helpful votes 4 helpful votes
“A five star Inn”
5 of 5 stars Reviewed 3 April 2012
2
people found this review helpful

The innkeeper and the staff pamper their guest from the moment you arrive and through out you stay. The Inn it's self is lovely as are the guest rooms. The gourmet breakfast was out standing as was their coffee. The evening dinning experience was excellent. They have a very good wine list to choose from to complement your meal. Our... More

Was this review helpful? Yes
See 3 more reviews by Carol T for Ashland
WinchesterInn, General Manager at The Winchester Inn, responded to this review
6 April 2012

Thanks for the kind words! It is wonderful to hear that you enjoyed your stay. I know that our staff takes great pride in offering some of the finest lodging and service anywhere. Our Chef Billy is thrilled that you enjoyed yourselves. I am also happy to hear that you enjoyed the wine list. It is always a pleasure to... More

novato, CA
1 review
1 helpful vote 1 helpful vote
“classy joint”
5 of 5 stars Reviewed 29 March 2012
1
person found this review helpful

The Winchester Inn is lovely and the location is perfect. Breakfast was superb and the bar was lots of fun in the evening.They had a bourbon-cheese tasting the week we were there-something different! We walked two blocks to the playhouse and saw Animal Crackers-hilrious! The folks working at the Winchester are so nice. They pamper you, bringing snacks at happy... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
6 April 2012

Thank you so much for writing! I'm so glad to hear that you enjoyed the whiskey tasting! We are always trying to find new ways to excite. It is also wonderful to hear that you enjoyed the Queen Anne room. We actually just remodeled that bathroom along with two others. Hope you see you again soon. Regards, Drew Gibbs General... More

Carmel Valley, California, United States
1 review
1 helpful vote 1 helpful vote
“wish I could have stayed longer”
5 of 5 stars Reviewed 21 March 2012
1
person found this review helpful

We stayed at the Winchester Inn on a Saturday night while visiting friends in Ashland. Every detail of this charming B&B is impressive, from the cozy bedding and towels to the coconut macaroon goodies in our room when we arrived. We enjoyed the wine sampling in the comfortable wine bar and appreciated our server's knowledge of local and international wines.... More

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
22 March 2012

Thanks so much for writing! We can't wait till you come back as well! I would have to agree that the morning breakfast crew puts out an amazing spread. And, honestly there is not a lot that can beat a scrumptious meal while the outside world is being dusted with snow. You make an excellent point about the 2 beds... More

Eugene, Oregon, United States
1 review
1 helpful vote 1 helpful vote
“Lovely Experience”
5 of 5 stars Reviewed 11 February 2012
1
person found this review helpful

The Winchester Inn is a delightful place to stay! The room was elegant & comfy with a fireplace & sitting room. The service was impeccable as was the food & wine list. This will definitely not be my last stay.

Was this review helpful? Yes
WinchesterInn, General Manager at The Winchester Inn, responded to this review
9 March 2012

Thanks so much for joining us! We are always working to make sure the everything from the beds to the wine list are as perfect as possible. We can't wait for you to join us again! Regards, Drew Gibbs General Manager Certified Sommelier More

Travellers who viewed The Winchester Inn also viewed

The Village Suites at Ashland Hills
The Village Suites at Ashland Hills
4.5 of 5 stars 155 Reviews
Ashland, OR
Show Prices ABS:HotelCheckRates-d95891?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed
Ashland Springs Hotel
Ashland Springs Hotel
4.5 of 5 stars 237 Reviews
Ashland, OR
Show Prices ABS:HotelCheckRates-d225890?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed
Green Springs Inn
Green Springs Inn
4.5 of 5 stars 56 Reviews
Ashland, OR
Show Prices ABS:HotelCheckRates-d1103010?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewed
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

35 South Second St., Ashland, OR 97520
Price range (per night):* 251 AUD - 385 AUD

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

Travellers also viewed...

  • The Village Suites at Ashland Hills
    The Village Suites at Ashland Hills
    4.5 of 5 stars 155 Reviews
    Show Prices ABS:HotelCheckRates-d95891?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewedAboveFold
    Ashland, OR
  • Ashland Springs Hotel
    Ashland Springs Hotel
    4.5 of 5 stars 237 Reviews
    Show Prices ABS:HotelCheckRates-d225890?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewedAboveFold
    Ashland, OR
  • Green Springs Inn
    Green Springs Inn
    4.5 of 5 stars 56 Reviews
    Show Prices ABS:HotelCheckRates-d1103010?&src=Hotel_Review&fromServlet=Hotel_Review&Action=QC_AlsoViewedAboveFold
    Ashland, OR

Browse nearby

Hotels (19) | Restaurants (74) | Things to Do (23)
The Winchester Inn
35 South Second St.
Ashland, OR 97520
Get Directions
What's Nearby:
Click map pins for more information.
Interactive map
Call now to book: 1-800-45-HOTEL from hotels.com

Explore Ashland

Free Ashland Guide

Get your quick guide to the top hotels, restaurants and things to do.
 
Download your guide now!
Get it now
Bath Suite Winchester Inn and Restaurant by Rochelle Carr Sunset Room
The Winchester Inn Photos (18 traveller photos)

Hotels around Ashland

Explore the world
Hotels
Sightseeing
Restaurants
The Winchester Inn
Show the lowest price for this hotel (from our partners)
Show Prices