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“Delicious and Decadent” 5 of 5 stars
Review of The Winchester Inn

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The Winchester Inn
35 South Second St., Ashland, OR 97520   |  
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Hotel website
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Hotel amenities
Special Price
10% off room rate
Ranked #11 of 37 Ashland B&B and Inns
Ashland, OR
Senior Reviewer
9 reviews 9 reviews
3 hotel reviews
Reviews in 3 cities Reviews in 3 cities
3 helpful votes 3 helpful votes
“Delicious and Decadent”
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.

Room Tip: Every room is so lovely. If you want more privacy, choose the New Suite, Courtyard or Brighton.
See more room tips
  • Stayed August 2013, traveled solo
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, Owner at The Winchester Inn, responded to this review, April 10, 2014
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
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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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170 people have reviewed this hotel

Traveler rating
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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
California
Senior Contributor
24 reviews 24 reviews
11 hotel reviews
Reviews in 15 cities Reviews in 15 cities
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.

Room Tip: Enders room was towards the back with an extra single bed. Very quiet with a small patio.
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  • Stayed September 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, Owner at The Winchester Inn, responded to this review, April 10, 2014
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
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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Contributor
11 reviews 11 reviews
7 hotel reviews
Reviews in 9 cities Reviews in 9 cities
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 the Shakespeare theaters!!!! Wonderful stay.

  • Stayed August 2013
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, Owner at The Winchester Inn, responded to this review, April 10, 2014
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
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
maryland
Contributor
18 reviews 18 reviews
9 hotel reviews
Reviews in 12 cities Reviews in 12 cities
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed September 2, 2013

Located in a charming Oregon town, just a five minute walk from the Shakespeare Festival complex, the Winchester offers a fine mix of comfortable accommodation, superior cuisine and top-line Oregon wines. Rooms are spacious, not overburdened by the twee Victoriana so common in East Coast B&Bs. Staff and owners -- all personable and helpful -- operate the Winchester as a boutique inn so there's no forced interaction with other visitors, and the restaurant attracts guests from the Inn and from without.

Rooms, of course, vary. Ours was well-maintained and comfortable but perhaps not one of the best in house.

I can't say the Winchester is the best in Ashland, because this was my first trip. Given that I'll almost certainly stay there again, that's a judgement I'm happy not to make.

  • Stayed August 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Palo Alto, California
Senior Contributor
41 reviews 41 reviews
18 hotel reviews
Reviews in 26 cities Reviews in 26 cities
27 helpful votes 27 helpful votes
4 of 5 stars Reviewed August 31, 2013

This B & B is only one and a half blocks from the Oregon Shakespeare Festival theaters. The room we had was spacious with a living room and bedroom. Happily, it had a refrigerator and makings for coffee and tea. The bathroom has been updated, though the shower does not have a grab bar. With quite a few older people staying here, it would be a good addition. The bed is very comfortable with lovely linens. The other furniture, though, is a bit tired.
The turndown service was not as consistent as it should be. One night, only the bed was turned down, but nothing else was tidied.
The staff is very pleasant and helpful.
The breakfasts are visual and taste treats, with attentive service.
Though a person with a cane or walker could manage, there are stairs to the bar and restaurant and to a number of the rooms.

  • Stayed August 2013, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Portland, Oregon
Top Contributor
58 reviews 58 reviews
13 hotel reviews
Reviews in 14 cities Reviews in 14 cities
13 helpful votes 13 helpful votes
4 of 5 stars Reviewed August 14, 2013

There were a number of nice touches in the room. It is an older property, so I think they've done pretty well with it. A bit of an awkward walk to the dining room in the rain. We lucked out in being able to park near our room, but I could see that we easily could have had to walk quite a distance had we not. We ordered a cheese plate in our room. I thought it was lovely, nice cheeses.

  • Stayed April 2013, traveled as a couple
    • 3 of 5 stars Value
    • 5 of 5 stars Location
    • 3 of 5 stars Sleep Quality
    • 4 of 5 stars Rooms
    • 4 of 5 stars Cleanliness
    • 4 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Redding, CA
Senior Reviewer
6 reviews 6 reviews
6 hotel reviews
Reviews in 5 cities Reviews in 5 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed August 13, 2013

We stayed in the Catharine M room. Second story in the heritage bldg. The room & bath were very spacious and super clean. It had a balconly (however, it's shared with the room next door, so not private, if that matters to you). The queen bed was very comfortable and the linens were very high quality. The hotel was full, but you never heard anyone from the room. Great insulation. Very attentive, nice staff. They deliver sweets to your room in the afternoon, and also offer turn down service. The hotel bar is top notch. Say "hi" to Owen the mixologist. The included breakfast was unique and very delicious too. They truly take everything to the next level at the Winchester Inn and still maintain that friendly, unpretentious atmosphere. We've already booked our next stay!

  • Stayed August 2013, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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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 37 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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