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The Winchester Inn

Certificate of Excellence
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35 South Second St., Ashland, OR 97520
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The Winchester Inn
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193 reviews from our community

Traveler rating
    166
    19
    3
    2
    3
See reviews for
22
117
7
9
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    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 (44)
Date | Rating
  • English first
  • French first
  • Any
English first
  • All months
    (193)
  • Mar-May only
    (51)
  • Jun-Aug only
    (62)
  • Sep-Nov only
    (56)
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    (24)
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There are newer reviews for The Winchester Inn
See the most recent reviews
Boston, MA
2 reviews
6 helpful votes 6 helpful votes
4 of 5 stars Reviewed July 28, 2009

We stayed at the Winchester for our first-ever trip to Ashland for the Oregon Shakespeare Festival. We'd read some good reviews online and the location was convenient so we booked several months ahead. We really enjoyed the Inn, would stay again with no hesitation and would recommend it to others. - The innkeepers (Laurie and Michael) are very nice and... More 

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Danville, CA
1 review
5 of 5 stars Reviewed July 13, 2009

I've been staying at the Winchester Inn for my annual trip to the Oregon Shakespeare Festival for about 10 years. (And for about 8 years before that I strolled by the Inn on each visit and gazed longingly at it's Victorian ginger-bread, English gardens, and romantic gazebo.) The Inn is right in the heart of Ashland. I park the car... More 

Was this review helpful? Yes
WinchesterInn, Manager at The Winchester Inn, responded to this review

I'm so glad that you found us. It is always a pleasure to have you stay, and we will look forward to your next trip with more culinary delights waiting. I'll be sure to let the kitchen staff know how much you appreciate their food and presentations. Best regards, Drew Gibbs More 

South Florida, Florida
Top Contributor
101 reviews 101 reviews
12 hotel reviews
47 helpful votes 47 helpful votes
5 of 5 stars Reviewed July 13, 2009

Well located. Very good room. Very good bed. Very good food. Very nice service.

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Brookings, Oregon
1 review
5 of 5 stars Reviewed July 10, 2009

We love everything about the Winchester. The breakfast selection and quality is the best we've ever had. The location is perfect for the OSF plays and restaurants. The management and staff go out of their way to make us feel special. Also, the wine bar is really great. The rooms are all clean and very comfortable. What more can you... More 

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California
1 review
5 of 5 stars Reviewed July 9, 2009

Location is ideal. The Barbara Howard Street is spacious and enjoyable. Breakfast is delicious and the service more than gracious.

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Rural SC
Top Contributor
63 reviews 63 reviews
13 hotel reviews
21 helpful votes 21 helpful votes
5 of 5 stars Reviewed July 5, 2009

This was our second time at the Winchester,and we enjoyed it just as much this time as in 2007. The Inn is three adjacent Victorian houses and gardens that have been converted to a lovely, welcoming Inn. The rooms are well appointed and comfortable, the shower was *great* and the bed was really comfortable with lovely linens and down comforter.... More 

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Toronto, Canada
Top Contributor
149 reviews 149 reviews
15 hotel reviews
155 helpful votes 155 helpful votes
5 of 5 stars Reviewed July 2, 2009

We had a wonderful stay at your inn. It's a very charming inn, very comfortable, friendly and helpful staff, and your restaurant was excellent. Our only regret is we couldn't stay longer. We wouldn't hesitate to stay at the Winchester Inn if we return to Ashland (a beautiful area) and would recommend it highly to anyone

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Lahaina Maui
Reviewer
3 reviews 3 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed June 30, 2009

The Winchester is our place when we attend the Oregon Shakespeare Festival. Just a short, two-minute walk, from the festival trio of theaters, the Winchester has it all: fanciful but totally modern rooms, attentive staff and oh, those breakfasts. If you are tempted by the scrumptious scones, muffins and artfully presented fruits, keep in mind that if you don't want... More 

Was this review helpful? Yes 1
California
1 review
5 of 5 stars Reviewed June 29, 2009

Staying at the Winchester Inn is an experience you will never forget. It's the perfect blend of relaxation and fun. My friends and I have been traveling to Ashland for an annual get together for the past 21 years. We have stayed at various places over the years (other B&B's and hotels) until we happened upon The Winchester Inn. From... More 

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Woodland, California
Top Contributor
52 reviews 52 reviews
15 hotel reviews
133 helpful votes 133 helpful votes
5 of 5 stars Reviewed June 26, 2009

A group of girlfriends have been going to Ashland for about 20 years, and after we discovered the Winchester Inn we never even considered staying anywhere else. We look forward to the leisurely breakfasts in the beautiful dining room (the scones on Sunday are to die for!), the beautiful rooms and soft beds, and the warm hospitality of Laurie and... More 

Was this review helpful? Yes
WinchesterInn, Manager at The Winchester Inn, responded to this review

Thank you for the kind words. It is always a pleasure to have you return. We'll be sure to have something wonderful waiting for you when we see you next year. Regards, Drew Gibbs More 

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