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“Charming Inn”
Review of The Winchester Inn

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The Winchester Inn
Ranked #8 of 31 Ashland B&B and Inns
Certificate of Excellence
San Mateo, CA
Level 4 Contributor
33 reviews
9 hotel reviews
common_n_hotel_reviews_1bd8 18 helpful votes
“Charming Inn”
Reviewed September 4, 2012

We have been going to the Ashland Shakespearean Festival with friends for over 20 years and have stayed in several inns. The Winchester Inn is by far the best. The ambiance of this Victorian inn is wonderful as are the breakfasts and dinners. This family-run inn is well-maintained, and it has won many awards. The only downside is that it has become a bit expensive, but this is true for most Ashland lodging. If you stay or eat there, you won't be disappointed.

  • Stayed September 2012, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank TravelTrekker1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks so much for writing! It is wonderful to hear that you have enjoyed your stays with us. We understand that staying in Ashland can be pricey. As such we regularly offer specials as well as have taken a new look at our pricing structure for next year with the thought of being able to offer a wider range of prices. We do recognize that we are a independently owned boutique property and as such, our prices will always be above those of a chain. What we strive to do is offer extra amenities to make all of it worthwhile. Thanks again for writing!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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239 reviews from our community

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Rating summary
  • Location
  • Sleep Quality
  • Rooms
  • Service
  • Value
  • Cleanliness
Traveler tips help you choose the right room.   Room tips (57)
Date | Rating
  • English first
  • French first
  • Any
English first
washinton wv
Level 1 Contributor
4 reviews
4 hotel reviews
Reviewed August 27, 2012

Stayed1 nite at the Winchester. Our room was nice but they should think about replacing the stained and dirty looking carpet. Beds were comfy and breakfast was delicious. Would consider staying there again.

  • Stayed August 2012, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Tom E
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks so much for writing! I'm glad you were comfortable! As to the carpets we are aware and have just had most of them go through deep cleaning. Every year we pick three or four rooms to get a face lift. Thanks for letting us know. We will be sure to get those taken care of asap.

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Portland, Oregon
Level 6 Contributor
132 reviews
21 hotel reviews
common_n_hotel_reviews_1bd8 49 helpful votes
Reviewed August 26, 2012

When going to the Oregon Shakespeare Festival there is no better place to stay. It is conveniently located less than two blocks from the three stages. the rooms are clean, spacious and luxurious. The staff and the owners are warm, inviting and helpful. The food is delicious and amongst the best in the Ashland with the breakfast being anything you could want. They go out of their way to accommodate. Their dinners are also superb but difficult to squeeze in if you are going to theater. Most of their guests are repeaters. We have been there for more than five years. We also meet some of the nicest people.

Room Tip: They have a limited number of rooms with a king bed. They have many with extra beds.
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  • Stayed August 2012, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank restats
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks for joining us again! It can be a squeeze to make the play if you are thinking of a nice leisurely dinner. We generally suggest at least two hours to make sure that everyone gets to the show on time. Hope to see you again soon!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Gig Harbor, Washington
Level 2 Contributor
5 reviews
Reviewed August 14, 2012 via mobile

Once again we enjoyed a lovely four days at the Winchester Inn. The rooms are more than comfortable...love the newly renovated bathrooms and the fabulous beds. The breakfasts are delicious and beautifully presented. As mentioned by others....do have dinner at the inn at least once during your stay. Tasty, beautiful and a good value. Don't miss the bar...a most gracious spot to unwind a bit. The bartender is a delight!! All the staff...and the owners...go above and beyond to make your stay memorable. Already booked our visit for 2013!!

Stayed August 2012, traveled with friends
Helpful?
Thank Linda C
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks for joining us again! I am thrilled to hear that you enjoyed spending time in the bar with Eoin, our bar manager. We all agree that he is a fantastic addition to the Inn. Looking forward to seeing you again next year!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Santa Barbara, Calif
Level 6 Contributor
187 reviews
93 hotel reviews
common_n_hotel_reviews_1bd8 114 helpful votes
Reviewed August 14, 2012

Reasons for liking the Winchester Inn:
1. A unique hotel, the only cookie cutter is in the kitchen. Each room is different and therefore the several rooms may appeal to a wide variety of desires. We have been staying in this hotel at least annually for many years..... and quite frankly enjoy it as much as almost any hotel anywhere. In earlier years we had stayed in other places in Ashland, and there are many. But we now just book in at the Winchester. What is not to enjoy with the small afternoon snack delivered to the room, the turn down service, the fluffy towels and all the amenities of a first class hostelry in a true theatre town.
2. The hotel is Family run by a very professional team. We have had good suggestions about restaurants, though there is one in the Hotel. The grounds are beautifully landscaped and maintained. We have seen family members setting flower beds in the spring, and the "crew" tending them all summer long. Sitting with friends with complimenary coffee in the Gazebo or on the porch in the morning makes catching up with our friends who come from several points of the compass most enjoyable.
3. Restaurant. The complimentary breakfast choices are wide, and one can order additional items. (They do request that you leave a tip for the excellent service).
We had two really good dinners on our last trip, and have found the quality of the cuisine and variety to be amongst the best in Ashland. (As might be expected, there are many Ashland restaurants, but the quality of the more expensive ones is rather spotty.) Tables are suffiently spaced and the room is reasonably quiet so that conversation is possible.
4. The Oregon Shakespeare Festival is 2 blocks away.
5. Hiking. We invariably find new and interesting hiking opportunities without using our car. Lithia Park extends upstream on the Ashland Creek from the Festival Theatre complex and a walk in Lithia Park is our mandatory first treat.... the trail is fairly flat, meandering upstream along the creek which is bounded by beautiful plants and trees. This walk is suitable for any fitness level. Above this park there are access routes into the mountains, ultimately linking with the Pacific Crest Trail, if that is one's goal. We have found several different routes and trails and also enjoy walking in the Ashland neigborhoods.
6. Ashland is the home of the University of Southern Oregon. A walk to and around the campus is also accessible to any fitness level.

Room Tip: The very helpful staff can help one choose the right room. If you like light, there are rooms with l...
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  • Stayed August 2012, traveled as a couple
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
1 Thank Oski80
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Wow! Thanks for the glowing review! All is true, but if there is ever anything we can do better, please let us know! It was a pleasure having you, and I hope that we have the chance to have you back soon!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
Nevada
Level 5 Contributor
97 reviews
31 hotel reviews
common_n_hotel_reviews_1bd8 58 helpful votes
Reviewed August 12, 2012

We were impressed. We stayed here for four nights and were sad to go home so soon. The inn is small enough so that the staff come to know their guests during their stay. We stayed on the second floor of the Heritage House and found our room to be very comfortable and clean. Our room shared a small patio with another room and was pleasant for reading and relaxing. It faced the main house and looked over into the garden making it a quiet retreat. The pastries in the afternoon were a nice touch as were the caramels with the turndown service. The bed is very comfortable. There was a sofa bed in the room also but did not use it for sleep so am not sure how comfortable it would have been.
We enjoyed the complimentary breakfasts very much and didn't really need to eat another meal until dinnertime. Homemade pastries and fruit followed by your choice of breakfast entree. We enjoyed one dinner a the restaurant as well and found it equally superb.
I highly recommend staying at the Winchester Inn or, if not that lucky, to enjoy dinner here. I look forward to our next stay here.

  • Stayed August 2012, traveled with friends
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank NevadaSoulTrain
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks so much for the kind words! It is always wonderful to hear that you enjoyed your stay. The staff all take great pride in being able to offer the kinds of service that we do. And the kitchen, in particular, takes great pride in the meals they present. I hope you have a chance to join us again next year!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
San Luis Obispo, California
Level 5 Contributor
60 reviews
8 hotel reviews
common_n_hotel_reviews_1bd8 23 helpful votes
Reviewed August 10, 2012

We love this place and look forward to what has become our annual visit. Warm welcome, personal attention, lovely accommodations--what more could you ask for? The breakfasts are superb; you won't want to eat again until dinnertime. But do plan to have dinner here as well, because it's also superb.

Room Tip: We like the Marjorie Roy room. It's upstairs on the corner with a nice sitting area, nice views...
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  • Stayed August 2012, traveled with friends
    • Value
    • Location
    • Sleep Quality
    • Rooms
    • Cleanliness
    • Service
Helpful?
Thank Michael S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
WinchesterInn, General Manager at The Winchester Inn, responded to this review, September 5, 2012
Thanks for sharing! We are thrilled to hear that it is becoming a yearly event. The majority of our guests are those who join us year in and year out. The more familiar faces the better. We hope to see you again next year!

Regards,

Drew Gibbs
General Manager
Certified Sommelier
Report response as inappropriate
This response is the subjective opinion of the management representative and not of TripAdvisor LLC.
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Additional Information about The Winchester Inn

Property: The Winchester Inn
Address: 35 S 2nd 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 #8 of 31 B&Bs / Inns in Ashland
Price Range (Based on Average Rates): $$$
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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