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The Winchester Inn

35 South Second St., Ashland, OR 97520
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Best prices for: 1 room 1 guest
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Certificate of Excellence 2014
The Winchester Inn
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The Winchester Inn
The Winchester Inn
The Winchester Inn
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189 reviews from our community

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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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Berkeley, California
17 reviews 17 reviews
8 hotel reviews
11 helpful votes 11 helpful votes
3 of 5 stars Reviewed 1 week ago

We recently stayed 3 nights at the Winchester Inn. We had beed at the hotel last spring to purchase wine from their shop and had visited two rooms in the main building and were looking forward to being able to stay there this month. Unfortunately, our room did not live up to our expectations. Here are the issues we had... More 

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2 reviews
5 of 5 stars Reviewed 3 weeks ago

We were staying in the 'new suite', it is a remodeled small unit, not part of the main house. The exterior appearance is unimpressive, however once inside we were impressed with coziness of both bed rooms and living room. Love the stay, and definitely will stay with the inn next trip.

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Senior Reviewer
8 reviews 8 reviews
3 hotel reviews
10 helpful votes 10 helpful votes
5 of 5 stars Reviewed 3 weeks ago

This was really a wonderfull New Years eve. The inn is quaint clean and the service was impeccable. Truly a perfect place for a romantic getaway for couples. Ashland itself we found clean and friendly.

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Victoria, Canada
Senior Contributor
33 reviews 33 reviews
10 hotel reviews
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We recently stayed at the Winchester on two separate ocassions and both times we were impressed with the quality of our room - we opted to stay in the same room on both visits - and the spectacular breakfasts. The service was great and we really appreciated the cookies and macaroons. We are already looking forward to our next visit.

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Florence, Oregon
Senior Contributor
36 reviews 36 reviews
14 helpful votes 14 helpful votes
4 of 5 stars Reviewed December 3, 2014

My husband and I stayed at this Inn for the first time just before Thanksgiving; this was low season & prices for the rooms are pretty good. We stayed in the Fordyce suite; beautiful bathroom with a 2 person spa & shower. Comfortable room with a view of the gazebo. It's in the main house so there was a little... More 

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Los Angeles, California
17 reviews 17 reviews
10 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed November 13, 2014

We spent a long weekend at the Winchester in Ashland this November. We stayed in the Barbara Howard room in the annex house next door to the Inn. It was on the 3rd floor in the back so It was spacious, quiet, had a large bathroom with a spa tub and a fireplace in the living room! Breakfast was included... More 

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chicago area
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
23 helpful votes 23 helpful votes
5 of 5 stars Reviewed November 10, 2014 via mobile

What a fantastic experience we had at The Winchester Inn last night. The Inn is beautiful - not only the exterior but the interior room design and decor. We stayed in the Garden room and were impressed with the view, the lovely Bells of Ireland wallpaper and matching window sheers and the beautiful bed and furnishings. We thought someone was... More 

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Los Angeles
12 reviews 12 reviews
5 hotel reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed October 18, 2014

The Winchester Inn is so famous for their lovely accommodations, world class personal service, and five star restaurant (Alchemy), they really don't need another rave review from me. I would like to confirm here what others have said about this heart-of-Ashland gem. Walking distance from OSF theaters, slightly off the main street but in the heart of town, this quiet... More 

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Glenn, Michigan
3 reviews 3 reviews
4 of 5 stars Reviewed October 1, 2014

Great accommodations, top rate service, beautifully decorated, ideally located, and an historic property. What a great package. And don't forget Alchemy Restaurant. A five star experience all around. We'll be back!

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2 reviews
5 of 5 stars Reviewed September 21, 2014 via mobile

The New Suite is awesome for a family with kids. Amazing stay! Beds are amazingly comfortable. We feel so pampered. Truly an extraordinary experience. The customer service was top notch. Breakfast was delightful. After 30 years of various B&B experiences in Ashland, this one scores in the very top.

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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
Price Range (Based on Average Rates): $
Number of rooms: 20
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