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“A Gem of an Inn in an Oregon cultural center” 5 of 5 stars
Review of The Winchester Inn

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The Winchester Inn
35 South Second St., Ashland, OR 97520   |  
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Hotel website
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Hotel amenities
Ranked #10 of 36 Ashland B&B and Inns
Washington DC
1 review
“A Gem of an Inn in an Oregon cultural center”
5 of 5 stars Reviewed December 16, 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 priority.
The included breakfasts in the dining room are delicious and beautifully presented. In the evenings the dining room morphs into a desitination restaurant and the wine bar provides a congenial place to meet other guests and sample Oregon's fine wines. The hosts and staff are exceptionally welcoming and helpful.

  • Stayed August 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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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 review, March 23, 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
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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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185 reviews from our community

Traveler rating
    159
    19
    2
    2
    3
See reviews for
20
111
7
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Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (38)
Date | Rating
  • English first
  • French first
  • Any
English first
Atlanta
Reviewer
4 reviews 4 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed December 16, 2012

We have stayed at this in multiple times and have loved it! The rooms are elegantly decorated and comfortable. The beds are so plush and the pillows were so wonderful that I researched them and bought some for our home. The breakfast contends for the best food in Ashland and their staff is very friendly. We will definitely be staying here again.

  • Stayed November 2012, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Santa Rosa, California, United States
Reviewer
3 reviews 3 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed November 26, 2012

This was our first visit to Ashland and we were unsure what to expect, but initially chose the Winchester Inn for its convenient location (within walking distance from the Shakespearean Theater, downtown shops, and Park). We hoped to find it inviting and peaceful. Our expectations were far surpassed as we enjoyed not only a warm, comfortable suite, but the quiet, peaceful atmosphere of this beautiful Victorian B&B. We felt as if we had stepped into the past with much of the decor, yet our room came fully equipped with TV and wireless service and luxurious bedding. We do not hesitate to recommend the Winchester Inn and its friendly staff to anyone looking for cozy, comfortable, convenient, and cost-effective accommodations.

  • Stayed November 2012, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Lafayette, California
Senior Reviewer
8 reviews 8 reviews
3 hotel reviews
Reviews in 4 cities Reviews in 4 cities
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed November 15, 2012

We now have stayed at the The Winchester three times and have loved it every time. The rooms are interesting, well-appointed and comfortable and the included breakfast is outstanding. Its location two blocks from the theaters and a half a block from downtown could not be better. We literally did not move our car the two days we were there.

Room Tip: Check the website for room descriptions as all are different.
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  • Stayed November 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Arcata, California
1 review
5 of 5 stars Reviewed November 14, 2012

A very nice B & B. Wonderful breakfasts and great service; we had a small issue with our room and they immediately moved us to an upgraded room while they addressed the problem. Location can't be beat.

  • Stayed May 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
California
Senior Contributor
25 reviews 25 reviews
10 hotel reviews
Reviews in 12 cities Reviews in 12 cities
9 helpful votes 9 helpful votes
5 of 5 stars Reviewed November 5, 2012

The Winchester Inn was a perfect B&B. It's a charming Victorian, every room unique. Outside are well-kept gardens and cozy reading spots. Breakfast is inventive and delicious, and so generous a meal that we never bothered to eat lunch during our three-day stay. There is also an afternoon/evening wine bar staffed by knowledgeable staff, and they serve dinner should you wish to dine at the inn. The proprietors were welcoming and helpful, a family atmosphere. Every afternoon they somehow managed to slip a small complimentary surprise treat into our room. Our room was one of the simpler ones, but still quite spacious, including a very comfortable bed, couch, and window seat looking out into the trees. The bathroom was clean and well-appointed. The Oregon Shakespeare Festival is a block away. Having discovered this delightful place, we will want to return to Ashland just to stay here!

Room Tip: We stayed in a modest room and it was GREAT.
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  • Stayed July 2012, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Sf
Senior Reviewer
10 reviews 10 reviews
5 hotel reviews
Reviews in 7 cities Reviews in 7 cities
5 helpful votes 5 helpful votes
4 of 5 stars Reviewed September 8, 2012

We've gone to the Oregon Shakespeare Festival for several years now, staying in a variety of places, but this year we found the place we'll go back to over and over again. Our room was spacious and comfy, the high bed with steps to climb in was charming, the bathroom clean and functional with lots of room and the breakfasts delicious and more than ample. The one dinner we had there was excellent, comparable to most high end restaurants even in San Francisco, and the staff and owners friendly and very helpful. They became grandparents today and we wish them lots of joy!! It is costly but offers a great deal in return. The only thing I wish they had was a tea or sherry in the afternoon and coffee or tea in the evening when we return from a play. Hope to see you again next year!!

Room Tip: I wish I knew.
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  • Stayed September 2012, traveled with friends
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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Additional Information about The Winchester Inn

Address: 35 South Second 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 #10 of 36 B&Bs / Inns in Ashland
Price Range (Based on Average Rates): $
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 
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