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All 38 Ashland B&Bs / inns

The Winchester Inn

35 South Second St., Ashland, OR 97520
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The Winchester Inn
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Ranked #10 of 38 Ashland B&B and Inns
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 1 week ago
Mshanti74 Portland, Oregon
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169 people have reviewed this hotel

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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 (31)
Date | Rating
  • English first
  • Any
English first
Portland, Oregon
17 reviews 17 reviews
9 hotel reviews
17 helpful votes 17 helpful votes
5 of 5 stars Reviewed 1 week ago

My husband and I were very impressed with the Inn. We stayed for one night during the Shakespeare Festival and were sorry we were not staying longer. The Inn is in a great location and a very short walk to the theater and the shops. The property is absolutely beautiful. Great landscaping, gazebo, and seating areas that create a little... More

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Mount Dora, Florida
1 review
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed 1 week ago

Let me say right away that, unfortunately, we were not able to visit the Inn for the two nights we reserved in July. My rating is based on our experience attempting to get at least a partial refund of our deposit after we were forced to postpone our trip to the northwest due to family issues. Be aware that if... More

Was this review helpful? Yes 1
Washington DC, District of Columbia
Top Contributor
135 reviews 135 reviews
31 hotel reviews
54 helpful votes 54 helpful votes
5 of 5 stars Reviewed 2 weeks ago

The Winchester Inn is a lovely old collection of Victorian homes, gathered together on a hilly street up from the main street, with a superb restaurant, the Alchemy. The Inn is very well staffed, the rooms are finely appointed and staff goes out of its way to learn your name and room. The bar is a lot of fun and... More

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Santa Barbara, Calif
Top Contributor
109 reviews 109 reviews
63 hotel reviews
63 helpful votes 63 helpful votes
5 of 5 stars Reviewed 3 weeks ago

The Gibbs family really make one's stay here remarkable. We have been coming back for many years and will continue to do so. (We have booked for next year!) On this trip we had booked a room that was not our first choice, a function of booking a bit late. (There are a number of rooms, all a bit different).... More

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Santa Cruz, California
2 reviews
5 of 5 stars Reviewed 4 weeks ago

In June 2013 we went to Ashland's Oregon Shakespeare Festival for the first time and had dinner at the Alchemy Restaurant in the Winchester Inn on one of the evenings. We had a wonderful meal, enjoyed excellent service and liked the look of the inn very much. So, for our 2014 trip to Ashland at the end of June we... More

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Portland, Oregon
2 reviews
5 of 5 stars Reviewed 4 weeks ago

We stayed here on drive from Portland to Sacramento. I highly recommend this hotel and restaurant and bar. WiFi, parking, 2 blocks from Shakespeare. Fabulous dinner and bar. Breakfast was outstanding.

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19 reviews 19 reviews
9 hotel reviews
14 helpful votes 14 helpful votes
5 of 5 stars Reviewed June 10, 2014

We have been staying at the Winchester Inn for many years and always look forward to coming back for another visit. We are always welcomed by Michael, Laurie and now Drew to our comfortable and well-kept rooms. The inn is so close to the Shakespeare Fesitval theaters as well as the Oregon Cabaret Theater, we never need to move our... More

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Ashland, Oregon
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed June 8, 2014

We are locals. We love the atmosphere, staff and food. Downside is portions are skimpy and there is only one veggie option for non-meat eaters. Coffee is excellent. Service is excellent. We go back in spite of the downside, but urge them to add more veggie options and double the potato portions.

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18 reviews 18 reviews
13 hotel reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed May 27, 2014

This was our second trip to Ashland ( family member is in the OSF Company as an actor). We have done extensive research on B&B's and stayed last year at another site. We have also been to B&B's in many other cities. This was one of the nicest we've stayed in. Clean and comfortable rooms. Excellent breakfats. The gardens were... More

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Portland, Oregon
1 review
5 of 5 stars Reviewed May 16, 2014

The Winchester Inn is one of those very special places. The service is superb; the linens on the bed are silky; the food is delicious; the gardens are gorgeous, with flowers and flowering trees blooming all around; the guest rooms are beautifully appointed, many with windows looking out on the garden, the breakfast is several courses, all wonderful. And, it's... More

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WinchesterInn, Owner at The Winchester Inn, responded to this review

Happy anniversary! I am thrilled to hear that your stay was a memorable one. I keep hearing compliments about our gardens, and we have to thank our wonderful gardener Trisha for all her hard work. We hope to see you for next year! Regards, Drew Gibbs Owner More

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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): $$$
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Bar / Lounge Beverage Selection Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Restaurant Suites
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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