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“Best B&B ever”
Review of The Winchester Inn

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The Winchester Inn
Ranked #9 of 30 Ashland B&B and Inns
Certificate of Excellence
Reviewed September 20, 2008

We just completed our 2nd stay here for 2007 &2008 Ashland Shakespeare Festivals. We have traveled all over USA & twice around the world. Winchester Inn is a family operated Inn with restaurant. In all our travels.It ranks #1 We booked for next October & 1/2 the rooms were already booked. Owner took us on wine tasting tour of Applegate Valley where we discovered a varietal(Tempranillo) new for us
Highly recommend but book far in advance.

  • Stayed: September 2008
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1  Thank maxChicago_Illinois
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, Manager at The Winchester Inn, responded to this reviewResponded October 17, 2008

Thank you for the the kind words. We look forward to seeing you again next October. Maybe we can find a few new wines for you in the meantime.

Drew Gibbs
Manager

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227 - 233 of 243 reviews

Reviewed August 20, 2008

The Winchester has been our #1 choice for lodging in Ashland for many years and will to be our favorite destination for many years to come. Recently, we booked rooms for ourselves and family members. Through a complete oversight on OUR part we were one day late in arriving in Ashland. First, the proprietor called and sincerely inquired as to the well being of our family, since it was unusual for us to be absent on a long held reservation. Secondly, they booked two available rooms allowing us to extend our reservation through the days that coincided with our theater tickets. Not only were the rooms available, they upgraded our last night to suites. While we had to move the last day to complete our stay the Inn owner/operator and staff insisted on moving our bags and clothing for us.
My wife and I frequently travel to Ashland for plays, vacations and business. Over the many years we've stayed at a variety of Ashland's B&Bs, Inns and hotels. All have been enjoyable stays. However, accommodations other than the Winchester are always our second choice.
We always enjoy the excellent daily three course breakfasts, gourmet dinners and convivial wine bar pre/post theater libations, all provided by gracious and knowledgeable staff. This is an establishment owned and operated by individuals who are dedicated to great service to their guests as well as their community. We look forward to our next visit.

Stayed: July 2008
1  Thank reginy
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed March 1, 2008

My husband and I (mid- 40's---look much younger :) ) just returned from Ashland to go skiing over the long President's Day weekend from the San Francisco Bay Area. We stayed at the Winchester Inn for probably the 10th+ time and, as always, found it to be wonderful. Mike and Laurie Gibbs are two of the most gracious and humble people you will ever meet and they have a knack for finding and employing the nicest people. They will bend over backwards to see that you are comfortable and happy and that is why we keep coming back. They have a highly-rated wine bar (Andy runs the bar---nice, well-informed) and restaurant in the main building and the food is excellent. The breakfasts are bigger and better than just about any Inn or Large B&B my husband and I have stayed in (and that is quite a few as that is what we prefer---ones with extra amenities like this and top locations). The scones with special nutty butter are to die for.

As far as the rooms go, they are spread over 3 buildings on the property. One is historic Victorian, one is old Victorian, and one is recently built. I think we have probably stayed in (or at least seen) most if not all of them. They are all large, clean and well-appointed. Many of them are suites (or large enough to be suite-like anyway). A few have historic claw tubs versus others which have modern whirlpool tubs so you have to tell the front desk what you are looking for exactly.

As far as the location goes, everything is within walking distance. It doesn't get any better than this: 1/2 block uphill from the main shopping/dining strip; ~2 to 3 blocks to the Shakespeare theaters; ~7 or 8 blocks to the railroad/gallery district; ~3 blocks to Lithia Park w/stream and ice-skating (nice fairly long hike up Lithia Park); ~4 to 5 blocks to the library; 1 block to bus stop that takes skiiers/boarders to Mt Ashland if you are so inclined; 1 block to movie house and bookstore. For a small town there is quite a lot to do and is perfect for a long weekend. (I guess there is river rafting and golfing in the summer but we usually go skiing in the winter.)

The only possible negative for someone else (not for us) based our last trip was that a colony of beetles had taken to running up the exterior of the main building. I think the Innkeepers were trying to figure out what to do with them--kill them or let them be. They are harmless, but if you are a bug-a-phobic, you might want to ask about the current status of them.

Other than that, I would say this is one of the best small Inns we have stayed at overall and a very good restaurant. I have eaten at some very nice restaurants (French Laundry, Chez Panisse, etc) so I think my standards are fairly high though I am not a snob, impossible to please or OVERLY picky. I am normal picky.

  • Stayed: February 2008, traveled as a couple
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2  Thank murmaid
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, Dining Room Manager at The Winchester Inn, responded to this reviewResponded April 9, 2008

Wow, that was a comprehensive review. Thanks for the wonderful words. I'm glad to hear that you enjoyed your stay. As far as the beetles are concerned, we are trying to figure out a way to keep them away from the Inn, but nature is very persistent (and luckily they are only with us for a week or so each year). Hope to see you again.

Drew Gibbs

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Reviewed February 27, 2008

We had a second stay at the Winchester Inn tonight, and it was as great as the last time. There service was perfect, and the room (Eleanor Rose on the 3rd Floor) was huge and wonderful. This is one of our favorite little get-a-ways, and we used it this time as we are passing through to California. We napped in the afternoon, and after a great dinner at the Monet Restaurant (across the street), we ended up in the Wine Bar chatting with other travellers. This is a must for us as we transit south or north, and can't wait to come back.

  • Stayed: February 2008, traveled as a couple
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1  Thank grapdad
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed January 12, 2008

I am an Innkeeper from Northern California and traveled to this inn for a meeting. I was very impressed with the inn, the room, the food and the hospitality. The room I stayed in was recently remodeled. It was very comfortable, spacious and elegantly decorated. The updated look (no flowery wallpaper) and thoughtful amenities had me taking notes and asking questions with a mind towards incorporating some of their ideas in my place. Both meals we had at the Inn were spectacular and it was particularly encouraging to see the innkeepers' children taking such an active interest in the business. Seeing the second generation coming up and taking part gives me much hope for the future of innkeeping.

  • Stayed: November 2007, traveled on business
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3  Thank Travell0tz
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed November 19, 2007

Comfortable rooms (we have stayed in six different rooms), gracious and helpful staff, excellent food - definitely a 5-star, or even more, experience. You are welcomed with smiles and warmth, your room is serene, and your breakfast is amazing. On top of the lovely ambiance, the folks at the Inn do everything they can to make your stay a real pleasure. Our latest stay came at a time when I was on a fairly restricted diet, and I was given personal care by the kitchen staff. A truly delightful place to stay.

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4  Thank OregonWoodduck
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed November 9, 2007

I had the fortunate opportunity to visit Ashland and stay at this lovely property last weekend. This was a wonderful and impressive experience. Thank you!

Stayed: November 2007
2  Thank BoutiqueHotels
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 S 2nd St, Ashland, OR 97520-2877
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 #9 of 30 B&Bs / Inns in Ashland
Price Range: $167 - $441 (Based on Average Rates for a Standard Room)
Hotel Class:3.5 star — The Winchester Inn 3.5*
Number of rooms: 20
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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