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All 37 Ashland B&Bs / inns

The Winchester Inn

35 South Second St., Ashland, OR 97520
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Ranked #10 of 37 Ashland B&B and Inns
Certificate of Excellence 2014
A recent review
5 of 5 stars reviewed 1 week ago
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180 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
Traveler tips help you choose the right room.   Room tips (35)
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2 reviews
5 of 5 stars Reviewed 1 week ago 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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4 reviews 4 reviews
3 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

I am so glad I found out about The Winchester Inn. Our plans allowed only a one night stay & it only made me want to come back again. The Inn was charming, the staff professional, the location great. Our room was a comfortable size & nicely decorated. The next time I visit I will reserve a room on the... More

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Ashland, Oregon
Senior Reviewer
9 reviews 9 reviews
6 hotel reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

Six of us, 2 in the Marjorie Roy Room and 4 in the New Suite, had a wonderful stay at Winchester Inn in Ashland. At every turn, we were delighted by the high quality and attention to detail we experienced throughout our vacation at the Inn. A relaxing, first class experience in every way. Especially the new suite was a... More

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Portland, Oregon
Top Contributor
54 reviews 54 reviews
44 hotel reviews
66 helpful votes 66 helpful votes
4 of 5 stars Reviewed 3 weeks ago

We've stayed in several different B&Bs in Ashland, but this was the first time at The Winchester Inn. As far as the room goes, it was by far and away the best in Ashland that we've seen. The location is perfect with easy access to downtown, restaurants and the Shakespeare Festival venues. The room was large with a king size... More

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SF Bay Area
Senior Contributor
42 reviews 42 reviews
10 hotel reviews
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed 3 weeks ago

We drive up from the SF Bay Area each year to enjoy the fantastic theatre and atmosphere in Ashland, and ever since we found the Winchester, we've not looked to stay anywhere else. Laurie, Michael and now Drew do everything the way it should be, and their property is perfectly located to walk to plays, restaurants and downtown. There is... More

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Los Gatos
Top Contributor
270 reviews 270 reviews
86 hotel reviews
201 helpful votes 201 helpful votes
5 of 5 stars Reviewed 3 weeks ago

Because we booked only two weeks out in the high season we only had limited choices for rooms that were still available. Opted for the Sunset Room because it had a connected deck off the room. This is the smallest of the 20 rooms and though it was a bit cramped the large deck with table and chairs gave us... More

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Hillsborough, California
3 reviews 3 reviews
3 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 3 weeks ago

What a find! We drove up from San Francisco, for the festival, and expected to come upon something reasonable but regular. Somewhere to just rest. But the Winchester is the opposite: Extraordinary. This is an inn that's giving it's guests 150% effort from morning til their heads hit pillows. Our breakfast was scrumptious - the best eggs in years. Our... More

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Corvallis, Oregon
3 reviews 3 reviews
5 of 5 stars Reviewed 3 weeks ago

Excellent as always. Great location, wonderful buidling and furnishings, excellent service from wonderful people. Wouldn't stay any where else in Ashland (except when Winchester is fully booked, which is often in high season),

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New Hampshire
2 reviews
5 of 5 stars Reviewed 4 weeks ago

We have stayed at many excellent B&Bs and hotels in Ashland over the 25 years we have been attending the extraordinary Ashland Shakespeare Festival. However Winchester House is now at the top of our list. Rooms are excellent, service could not be more professional or accommodating, and the restaurant is one of the very best in a town with a... More

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Huntington Beach, California
Senior Contributor
32 reviews 32 reviews
9 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed August 10, 2014

Wonderful location: near theaters, downtown and restaurants. Delicious breakfast and gourmet dinners at their Alchemy restaurant are prepared with best local ingredients. Fine wine bar, rooms are air-conditioned and free Wi-Fi!! Owners and staff make you feel welcomed

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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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