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“A Beautiful Stay Waiting for You” 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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Shakespeare Package
Ranked #11 of 38 Ashland B&B and Inns
Richland, WA
Contributor
16 reviews 16 reviews
9 hotel reviews
Reviews in 11 cities Reviews in 11 cities
11 helpful votes 11 helpful votes
“A Beautiful Stay Waiting for You”
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 private balcony for relaxing in the morning, in the evening, or at any time one needs a break. The bed is a great old frame that, with a comfortable bedding set, raises the sleeping surface to waist level--a portable step is provided for climbing in at night. The Sunset room is accommodating, nicely decorated, and just right for size (not spacious). Other, larger rooms are available, but the prices rise sharply.

The staff is very hospitable and friendly, eager to assist the guests and always available. We felt like we were really appreciated and welcomed to the inn. Breakfast comes with the room. It is served in the dining room and the service staff acts like you are paying $35 for breakfast for two, not enjoying a complimentary breakfast. Seating is in the dining room, and the service is superb. We enjoyed the Belgian waffle, the fruit cup, the scrambled eggs, etc.--all presented very excellently.

The Winchester Inn presents a grand experience for the avid Oregon Shakespeare Festival participant.

Stayed October 2013, traveled as a couple
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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, 1 week ago
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 they are really taken well taken care of. I hope you get the chance to join us again for more fantastic plays at OSF, and even get a chance to explore the town in quieter times.

Regards,

Drew Gibbs
Owner
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155 people have reviewed this hotel

Traveler rating
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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
Manhattan Beach, California
Senior Contributor
26 reviews 26 reviews
20 hotel reviews
Reviews in 19 cities Reviews in 19 cities
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 made it appear they were all together. We were also on the very top floor of the second building and getting in/out of the room involved climbing 3 flights of very steep stairs. (ok for us but maybe not for someone not so mobile) The Inn itself and the grounds are very pretty - especially enjoyed the rooms they use for breakfast as they overlook the garden. My favorite part of staying at the Inn was the food! The breakfasts were incredible --- 2 courses --- one sweet, the other savory. My hats off to the pastry chef -- some of the best breakfast goodies I've ever eaten. Also enjoyed the sweet treats left in our room nightly during turndown service. The staff overall was nice but no one seemed to really put themselves out on our behalf. One of the reasons we enjoy staying at B&Bs is for the personal service and interaction and that was missing here. It felt more like a regular hotel. Overall it was a good experience - but for the price, I expected a bit more.

Room Tip: If you have trouble with stairs - make sure you ask for a room on a lower floor.
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  • Stayed October 2013, traveled as a couple
    • 3 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
Was this review helpful? Yes
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, 1 week ago
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 the photos online. We are currently in the midst of redoing our website and the photography to better represent the Inn and the rooms as both have changed and been updated.

It is also true that we are not a true B&B, more of an inn or boutique hotel. While we are family owned and operated business, we are unlike other small B&Bs in both our size, the number of overnight guests that we accommodate and the inclusion of our restaurant and bar, which also means no family style meals. I hope that you do join us again, knowing what we are, so that we can give you that amazing experience that you feel was not quite there.

Regards,

Drew Gibbs
Owner
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Grants Pass, Oregon, United States
Top Contributor
67 reviews 67 reviews
13 hotel reviews
Reviews in 23 cities Reviews in 23 cities
19 helpful votes 19 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 a sitting area . The bathroom was spacious with a large jetted tub. In room bar with splits of wine, and champagne. The complimentary coffee and tea were gourmet brands (local I believe) which was a nice touch. I have stayed in a number of bed and breakfast/ Inns of this type and what strikes me at Winchester is how immaculate the accommodations are - no musty smell or creaking floorboards. The only drawback of the Fordyce room for some people might be the stairs. Nothing outside the normal - just a standard flight of stairs with no elevator. The Inn has rooms on the ground floor. There are around 20 rooms in total that are housed in a few closely situated buildings. Each one appears very unique. The breakfast was excellent. I think there were 3 or four choices. Bloody marrys and mimosas are extra. Fairly close to the Shakespeare Festival and only a block away from the Oregon Cabaret Theater.

  • Stayed October 2013, traveled as a couple
    • 3 of 5 stars Value
    • 4 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.
WinchesterInn, Owner at The Winchester Inn, responded to this review, 1 week ago
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 works better. I hope you have a chance to join us again.

Regards,

Drew Gibbs
Owner
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This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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
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.
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  • 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
Was this review helpful? Yes
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, 1 week ago
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.
California
Senior Contributor
23 reviews 23 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
Was this review helpful? Yes
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, 1 week ago
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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Senior Reviewer
7 reviews 7 reviews
6 hotel reviews
Reviews in 6 cities Reviews in 6 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, 1 week ago
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
15 helpful votes 15 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.

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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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