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The Winchester Inn

Certificate of Excellence
Hotel website
35 South Second St., Ashland, OR 97520
Special Price
20% off room rate
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1 room 1 guest
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The Winchester Inn
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204 Reviews from our TripAdvisor Community

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Traveler rating
    177
    19
    3
    2
    3
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23
125
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
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  • English first
  • French first
  • Any
English first
  • All months
    (204)
  • Mar-May only
    (52)
  • Jun-Aug only
    (72)
  • Sep-Nov only
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    (24)
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reno
Level Contributor
14 reviews
5 hotel reviews
common_n_hotel_reviews_1bd8 6 helpful votes
5 of 5 stars Reviewed 3 weeks ago

The location of the Winchester Inn is perfect for the Shakespeare theatre and the downtown area. Our room was large, clean and very comfortable. The room was quiet, and the bathroom was large. Upon arrival we found a nice tray with cookies, and another one with small hors d'oeuvres in our room, we were celebrating my husbands birthday. The Winchester... More 

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carmel
Level Contributor
15 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 11 helpful votes
5 of 5 stars Reviewed July 22, 2015

We stopped in for just one night. should have made it much longer. Everything was so nice and the restaurant was excellent. The food and wine caused us to stay right there on property. We had a great time visiting with other guests in the bar. It was one of those special nights when traveling. The town had a power... More 

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Calgary, Canada
1 review
5 of 5 stars Reviewed July 21, 2015

Rooms in the main building are beautifully furnished with a spacious bathroom, luxurious soaps, and gorgeous antique style bed. Tip for families: There is a separate suite detached from the main building that is modern, and sleeps up to five. Breakfast is included and is absolutely delicious, unlike the fare of included breakfasts at most hotels. I highly recommended the... More 

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Concord, Massachusetts
Level Contributor
52 reviews
18 hotel reviews
common_n_hotel_reviews_1bd8 28 helpful votes
5 of 5 stars Reviewed July 17, 2015

We've been going to the Oregon Shakespeare Festival once a year for about 10 years and return to The Winchester Inn. Laurie and Michael Gibbs warmly welcome all guests and the staff is also great. The rooms are sumptuous, clean and very comfortable. Love the beds! Breakfasts are deliciously decadent. Ashland is a great town with lots of shops and... More 

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Washington DC, District of Columbia
Level Contributor
174 reviews
34 hotel reviews
common_n_hotel_reviews_1bd8 55 helpful votes
5 of 5 stars Reviewed July 10, 2015

This was our second visit to the Inn. It's first class, of course, but I think the most important thing for us is that it is right in the center of Ashland, within three blocks of the Shakespeare Festival and half a block from the main street. The owners go out of their way to make sure you are comfortable,... More 

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Sisters, Oregon
Level Contributor
17 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed June 19, 2015

Very comfortable. The"Sunsrt" room is not spacious at all, but has a wonderful deck to enjoy a complimentary desert and the sun going down against the mountains across the valley. We normally object to a Queen size bed, but this one was excellent. The included breakfast was outstanding..not only in quality, quantity, but the patio setting as well. Very helpful... More 

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Lexington, Massachusetts
Level Contributor
3 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed June 15, 2015

I surmised from online reviews that this would be a very special place, and I was not disappointed. The room was comfortable and clean, and the staff were exceptionally friendly and helpful. The Artisan Restaurant was likewise a great experience. There is no question we would stay there again, should we ever return to this lovely town.

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Chicago, Illinois
2 reviews
5 of 5 stars Reviewed June 14, 2015

The Winchester Inn is a lovely place to stay. The people are simply wonderful - friendly, helpful, efficient; the rooms are well-appointed and comfortable; and the food is superb. I'm not sure how many times I've stayed there over the years, but I think about 10 times. I've had several different rooms and all are nice. Eating a gourmet breakfast... More 

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Level Contributor
6 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 12, 2015

We stayed at the Winchester Inn for three nights while attending the Oregon Shakespeare Festival and had a wonderful visit. The family that runs the property (since the 70's) is lovely and are always around making sure everything goes well. The rooms are comfortable, breakfasts are delicious and the location can't be beat. Alchemy, the restaurant at the Inn, is... More 

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Palo Alto
Level Contributor
3 reviews
3 hotel reviews
5 of 5 stars Reviewed June 1, 2015

My wife and I travel all over the world and The Winchester is one best bed and breakfast we have ever stayed in. It's family run and we feel like we are part of their family. They even have a full time gardener to keep up the grounds.

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