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Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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.
We booked the two bedroom cottage with two king beds and two bathrooms plus a pill out sofa. The cottage is a separate small building off the parking lot alley. Although it doesn’t look like much from the outside the inside is a 5 star hotel. Comes with small fridge, coffee maker, microwave and all the amenities you’d expect from a top notch hotel. The area is surprisingly very quiet. No one above or near you. The best part is the complimentary breakfast which is gourmet! It begins with a scone with fruit curd and cream then you get a great selection of breakfast plates - French omelette or eggs Benedict or gravlax. Very impressive!! Easy free parking in the alley. Very knowledgeable and efficient house staff. Everyone was friendly. I would definitely stay again. We have zero complaints.…
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Date of stay: July 2023Trip type: Traveled with family
Room Tip:Book the cottage if you have a family of 4 or 5
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We really enjoyed our stay in the Eleanor Rose Suite. It was on the top floor of a Victorian house with dormer windows, so had lots of charming changes in the roofline. The room was large, with lots of space to move around and a sofa and comfy armchair for reading. We enjoyed looking down on the town of Ashland and the beautiful mountains beyond. The location was a few minutes from the Oregon Shakespeare Festival and downtown Ashland so we walked everywhere. We splurged in getting this suite and part of the reason was because of the extra convenience of EV charging at a nearby sister property. Upon our arrival, we learned they no longer leased that property, so no charging included…a bit of a disappointment. But there were so many thoughtful touches, the staff was so friendly, and the breakfasts so wonderful that we thoroughly enjoyed our stay.…
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Date of stay: June 2023
Rooms
Cleanliness
Service
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
I cannot express fully just how much we enjoyed our stay at the Winchester Inn. The room was perfect, and the bed and bedding are amazing. We enjoyed the service of the Inn whose staff made special treats available for my wife's birthday, accommodated us when we needed to get another half hour to check out, and helped us with local directions. A superb stay with a superb staff. We will be back again!
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Date of stay: December 2022
Value
Cleanliness
Service
Room Tip:If you have limited mobility be sure to ask for an accessible room.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We love the Winchester Inn for several reasons. The employees are friendly, caring, and professional. We’ve become friends with several of them and have remained in touch with them during these past years. The rooms are spacious and quaint at the same time. The breakfasts are always tasty and diverse. The Winchester Inn is in close proximity to the OSF theaters, nice restaurants, shopping, and coffee shops. In addition to staying here every year, we also always go to it’s restaurant (Alchemy)!!! Great food and service!!
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Date of stay: September 2022Trip type: Traveled with family
Room Tip:There are no elevators!!!!
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
The Winchester Inn Is so beautiful, comfortable, and luxurious! I stayed in the Belvedere room for 5 days and it was unbelievably comfortable and beautiful. The bed is ultra Lux with a soft and cozy feather bed and down comforter and the bed is triple sheeted so it felt all the more luxurious because it's all clean and fresh for each new guest and that is something special! I wish every hotel did this! It also had a jacuzzi tub with a separate shower and big soft and fluffy towels, a comfy couch, a small dining table and a window seat with a view of the beautiful courtyard. The location is the best that Ashland has to offer because it's two short blocks to Shakespeare and dead center for everything you could want in downtown Ashland. Breakfast is as excellent as everything else here with a breakfast menu that changed every single day that I was there and everything was made fresh, perfectly prepared and delicious. To say that I was impressed is an understatement. The staff here is just lovely as well and nothing seems too much trouble! They were charming and accommodating at every turn and very well informed about where to go what to do and where to eat, really impressive! If you are trying to decide where to stay in Ashland then book here because you won't regret it.…
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Date of stay: August 2022
Cleanliness
Service
Sleep Quality
Room Tip:The Belvedere room is lovely
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
The room was charming, the food delicious and the customer service was exquisite! Easy walk to both the Oregon Shakespeare Festival and Lithia park. We stayed for 3 nights and had a really cozy rest, good bay window for reading over the twinkle lights of the garden.
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Date of stay: June 2022Trip type: Traveled as a couple
Room Tip:Some parking around the back, breakfast was included and it was awesome! Delicious homemade...
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
We have been to Ashland many times and have always stayed at another well known hotel. This time we chose the Winchester Inn and we were very pleased with our stay. A very comfortable, spacious room with a large bathroom and an excellent on site restaurant, The Alchemy. Everyone on staff was very friendly and helpful and we really enjoyed everything about our stay. Highly recommend!
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Date of stay: March 2022
Value
Service
Sleep Quality
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
This hotel is a breath of fresh air in the area. We have stayed in the majority of the hotels in the area, both corporate and privately owned and $ to $$$$$ during multiple seasons and years. I can confidently say that the Winchester Inn is by far the most cozy and relaxing of them all. The care that the staff of a family owned business takes compared to a corporate hotel was abundantly clear as those who handled our stay were involved, caring, accomodating, motivated, well spoken and clearly intelligent. They handled our relatively spontaneous activities and uncertain check in time with grace and poise and were welcoming to my service animal. I could write pages of glowing praise, but I think the staff and owners would graciously tell me to spend time enjoying my vacation instead. That is the kind of energy they exude and the attitude of their service. Thank you Winchester Inn, we will be back and will never again stay in lackluster hotels as long as remain a place of respite and joy.…
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Date of stay: March 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
A wonderful place for a good rest, great food and gracious hosts, roughly halfway between Portland or Seattle and the San Francisco bay area. We have also stayed during the Oregon Shakespeare Festival and found the location and service to be perfect!
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Date of stay: January 2022Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
The Winchester Inn is located just a few blocks from shops and Waterstone Spa. They have updated to a contemporary decor (other B and B's are still stuck in the Victorian era). Our room was Sunset (though it faces east). It was spacious, had a small balcony, gas fireplace, and large walk in shower. Thoughtful details included quality glassware for wine/champagne/cocktails, an honor bar, and little pastries. The restaurant, Alchemy, was outstanding for dinner (and so convenient). A very good breakfast cooked to order was included, making it an even better value.
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Date of stay: January 2022
Value
Service
Sleep Quality
Room Tip:Choose downstairs if you have trouble with climbing stairs because stairs are steep.
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This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
$169 - $283 (Based on Average Rates for a Standard Room)
LOCATION
United StatesOregonAshland
NUMBER OF ROOMS
20
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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