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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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199 Reviews from our TripAdvisor Community

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Traveler rating
    172
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22
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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
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    (199)
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    (52)
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Sisters, Oregon
Level Contributor
16 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 9 helpful votes
5 of 5 stars Reviewed 1 week ago

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 2 weeks ago

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 2 weeks ago

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
5 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

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
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 4 weeks ago

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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Walnut Creek, California
Level Contributor
103 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 64 helpful votes
5 of 5 stars Reviewed 4 weeks ago

I was surprised to try a search for Artisan Restaurant at the Winchester Inn in Ashland and come up with nothing. Six of us dined there in May before going to an excellent play and we were WOWed by the service and the food. The restaurant had been recommended by several local residents and it proved to be superb. Had... More 

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Eugene, Oregon
Level Contributor
16 reviews
3 hotel reviews
common_n_hotel_reviews_1bd8 4 helpful votes
5 of 5 stars Reviewed April 20, 2015

The Winchester Inn has twenty rooms housed in two Victorian homes, a carriage house, and a new building. We have three wonderful stays over the past four years. A lovely breakfast starting with a sweet roll and fruit and then a choice from three entrees is included with the room. The dining room has large windows on three sides overlooking... More 

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Los Angeles, California
Level Contributor
12 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 15 helpful votes
5 of 5 stars Reviewed April 20, 2015

We were in Ashland, as so many are, for the Shakespeare Festival Theatre. The Winchester is the perfect location, an easy walk to the theater and a short stroll to the main area of restaurants and retail in Ashland. Remember this is an Inn, not a hotel, so it is very individual in its furnishings and amenities. It is cozy,... More 

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Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed February 11, 2015

My boyfriend and I came down to Ashland for a little birthday getaway. I have friends here and my mom lives just a couple hours away. We stayed at the Winchester Inn and thank goodness we did. First of all, Ashland is a beautiful little city, surrounded by stunning scenery, architecture and history. As is the Winchester Inn. The staff... More 

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Redding, California, United States
Level Contributor
10 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
5 of 5 stars Reviewed January 28, 2015

A great trip from start to finish. Beautifully decorated, very nice people who work there. The rooms are roomy and comfy. Nice amenities. Luxurious linens. Cookies every night. Walking distance to town and all the wonderful shops there.

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