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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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96%
Ranked #11 of 38 Ashland B&B and Inns
Certificate of Excellence 2013
A recent review
5 of 5 stars reviewed 4 weeks ago
ajswain Kenilworth, IL
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155 people have reviewed this hotel

Traveler rating
    132
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    2
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19
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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 (25)
Date | Rating
  • English first
  • Any
English first
Kenilworth, IL
Contributor
12 reviews 12 reviews
9 hotel reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 4 weeks ago

We stayed in the "New Suite" as well and loved every minute of it. It was wonderful to have our own building as the interior was like the perfect apartment and the 2nd bedroom looked onto a small patio, with privacy from the back of the bookstore. The windows were position high so we didn't even see the alley or... More

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

Thanks for joining us! I am thrilled to hear you enjoyed the "New Suite". Embarrassingly, we are still trying to come up with a proper name for the room. We also feel like it is everything anyone might need for a family or couple's getaway. Hope you have the chance to join us again soon! Regards, Drew Gibbs Owner More

Portland, OR
Top Contributor
169 reviews 169 reviews
72 hotel reviews
208 helpful votes 208 helpful votes
5 of 5 stars Reviewed February 16, 2014

This is the fifth time in this property. We stay in the Robert Gordon Suite, which suits us well, in the building next door to the main building. What impressed me most is the bed! The sheets were like silk, & the covers were heavy & warm! I slept like a baby. The breakfast the next morning oh OJ, Strawberry... More

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

Thank you for the kind words! We are working towards that #1 spot, but there are a lot of fantastic properties in town. I am so glad to hear that you enjoyed the sheets (we are rather partial to them, and do happen to have them for sale) as well as the breakfasts! Hope to have you back again soon!... More

Pasadena, California
2 reviews
2 helpful votes 2 helpful votes
3 of 5 stars Reviewed January 2, 2014

My wife and I booked two nights at the Winchester Inn based on the reviews and their website, which promised charm, sophistication, and relaxation. We rented "The New Suite," which judging from their photos, offered all of these things, with the added benefit of a lot of space. We were traveling with our two boys and liked that it had... More

Was this review helpful? Yes 2
WinchesterInn, Owner at The Winchester Inn, responded to this review

Thank you so much for writing! I am so terribly sorry that you felt fooled. It is not our intention to fool anyone, ever. We are a property of five buildings, the New Suite being one of those five. It is actually a historic property and part of the downtown historic block (it was a surprise to us too when... More

London
Contributor
18 reviews 18 reviews
14 hotel reviews
27 helpful votes 27 helpful votes
3 of 5 stars Reviewed November 25, 2013

We stayed here for one night. The location and the style of the property can not be faulted. However, the slightly dated interior (old/antique doesn’t have to mean tired looking) was a little disappointing. The room, while small, was fun and had a definite charm. However being in the main house above the kitchen at the back, meant that the... More

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

Thank you so much for writing! I am sorry that things did not live up to your expectations. The room in question is one of our smallest and does sit above the kitchen. The kitchen strives to make sure that everyone is aware of noise as to not disturb guests, and I am sorry that was not the case during... More

Richland, WA
Contributor
16 reviews 16 reviews
9 hotel reviews
11 helpful votes 11 helpful votes
5 of 5 stars Reviewed October 23, 2013

We were in Ashland, OR at the beginning of the month to see some plays and managed to get in to the Winchester Inn. Managed is the operative work as one must book a room selection well in advance. This place is just that popular. We stayed in our favorite, the Sunset room. It is well-appointed, comfortable and has a... More

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

Thanks for joining us again! I am glad we managed to fit you in as well. The funny thing is that it all revolves around the Oregon Shakespeare Festival. Once you slip into November things open right up (and prices drop). And thank you for the compliments to the staff! They take great pride in making sure everyone feels like... More

Manhattan Beach, California
Senior Contributor
26 reviews 26 reviews
20 hotel reviews
18 helpful votes 18 helpful votes
4 of 5 stars Reviewed October 18, 2013

We stayed for 4 nights in the Barbara Howard Suite -- our first trip to Ashland. The hotel is perfectly situated to walk everywhere in downtown Ashland including the theatre which we enjoyed on Friday night. Our room was nice although not exactly what I was expecting - the fireplace and sitting room were separated from the bedroom, the website... More

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

I am so glad to hear you enjoyed your stay in the Barbara Howard suite. We do have many stairs on property as we are built into historic buildings. But, as you said, we are always happy to help find a ground floor room that will work if mobility is an issue. I am sorry that you felt mislead by... More

Grants Pass, Oregon, United States
Top Contributor
67 reviews 67 reviews
13 hotel reviews
18 helpful votes 18 helpful votes
5 of 5 stars Reviewed October 15, 2013

We stayed in the Fordyce room. An excellent room in the main "house" for a romantic getaway. Spacious and beautiful is what comes to mind. All the modern conveniences of a 5 star hotel in this historic Inn. This room is upstairs past the front desk. It was a fairly large room with a fireplace (gas), a king bed, and... More

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

Thanks for sharing! We do everything we can to give you a unique experience while making sure that all the creature comforts of a five star hotel are available. All 20 rooms are indeed unique, and it is true that we do lack an elevator. We are, however, always happy to try and find a ground floor room if that... More

Ashland, OR
Senior Reviewer
9 reviews 9 reviews
3 hotel reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed September 30, 2013

This Inn is truly a jewel. The rooms are magnificently appointed, with every attention to detail. The complimentary breakfast is wonderful as well. The tables and presentation are finished off with fabulous service. The owners, Laurie and Mike have created an extravagant oasis in the middle of downtown Ashland. A treasure, to be sure.

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

I am so thrilled to hear that you enjoyed the stay! I will agree that my parents, Mike and Laurie, do a spectacular job setting the bar high for everyone. Thanks for sharing! Regards, Drew Gibbs Owner More

California
Senior Contributor
23 reviews 23 reviews
11 hotel reviews
8 helpful votes 8 helpful votes
5 of 5 stars Reviewed September 22, 2013

We stayed in the Enders room for two nights. The Inn is charming and the rooms, restaurant and bar are all well appointed. Only a block from downtown, but very quiet, the property is centrally located to everything, including Shakespeare theaters. An incredibly delicious breakfast was included with our room and all special dietary needs are accommodated.

Was this review helpful? Yes
WinchesterInn, Owner at The Winchester Inn, responded to this review

I am so glad you had a chance to join us! The kitchen does make some fantastic breakfasts, and are always happy to help when it comes to dietary needs. Thanks again! Regards, Drew Gibbs More

Senior Reviewer
7 reviews 7 reviews
6 hotel reviews
7 helpful votes 7 helpful votes
5 of 5 stars Reviewed September 3, 2013

My wife and I are experienced travelers. In 30 years of traveling in the US and abroad....the quality of the service is excellent. The Inn has an extremely professional and congenial wait staff. The king bedroom was perfect and the mattress very supportive. The complimentary breakfast was 5-star restaurant quality with impeccable service. AND location is only 2 blocks from... More

Was this review helpful? Yes 1
WinchesterInn, Owner at The Winchester Inn, responded to this review

Thank you so much for the kind words! The staff takes great pride in being able to offer such service. I hope you have a chance to join us again soon! 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
Amenities:
Bar / Lounge Beverage Selection Business Center with Internet Access Free Breakfast Free High Speed Internet ( WiFi ) Free Parking Restaurant Suites
Hotel Style:
Ranked #11 of 38 B&Bs / Inns in Ashland
Price Range (Based on Average Rates): $
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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