Winchester Inn: Luxury in Ashland, OR

winchester inn, ashland, oregon
It’s a rare occurrence when I visit a property more than once. Such was the case for the Winchester Inn, located in the quaint, yet hipster town of Ashland, Oregon. While I stayed at the family-owned and operated bed and breakfast in 2008, like a family, it has currently expanded to include five separate buildings.

The inn offers big city hotel luxuries, while still maintaining its small town charm. A member of Unique Inns, the property boasts five separate buildings, offering 20 one-of-a-kind rooms in the Larkspur Building, Main House, Heritage House, Carriage House and New Suite.

winchester inn, bed & breakfast, asland, oregon
Winchester Inn Sylvan Room. Photo © 2015 Nancy D. Brown

My room, Sylvan Room, located on the second floor of the main house, was a standard queen, overlooking the almond tree out front. The bay window seat makes for a cozy reading spot, while the loveseat does double duty as a sitting area and serves as a fold-out twin bed. The private bathroom features a walk-in tile shower. You’ll notice the sink rests inside the top of an antique dresser.

winchester inn, window seat, bed & breakfast
Make yourself at home at Winchester Inn. Photo © 2015 Nancy D. Brown

All rooms include Antica Farmacista bath amenities, 600 thread count sheets, down feather bed, pillows and comforters, bathrobes, hair dryers, complimentary wifi, air conditioning, fresh flowers from the garden, evening turndown service and an afternoon treat delivered to your room. Some rooms feature spa tubs and fireplaces.

quail, alchemy restaurant, winchester inn, oregon
Foodies will love Alchemy Restaurant. Photo © 2015 Nancy D. Brown

Foodies will appreciate the complimentary two course breakfast and Alchemy Restaurant and Bar. Chef de Cuisine William “Billy” Buscher offers creativity in every dish. The Dungeness crab salad with arugula, hazelnut oil, orange supremes, lemon saffron aioli and candied bacon ($15.) was light and flavorful as a first course. My main course of stuffed quail featured a semi boneless quail stuffed with black mission fig and pork veal sausage, sauteed in duck fat then baked. Caramelized fennel and Humboldt fog goat cheese white polenta was served alongside a sauce of fig and marsala, mounted with bone marrow butter ($29.) I had spied house made chocolate truffles in my room earlier, so I didn’t tempt myself with the dessert list, although the wide ranging bar menu offered plenty of libation temptations.

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bed & breakfast, winchester inn
Winchester Inn two course breakfast photo © 2015 Nancy D. Brown

Rates range from $250-$260 for the Sylvan Room during high season, with other rooms priced between $125-$275 depending on time of year. As always, check the website for current pricing.

Need to know:
The Winchester Inn is not pet-friendly.
Check in: 3:00 p.m.
Check out: 12:00 p.m

patio, winchester inn, ashland, oregon
Winchester Inn patio photo © 2015 Nancy D. Brown

Insider Tip: Centrally located in downtown Ashland, the inn is only two blocks from Oregon Shakespeare Festival and close to more than 50 wineries in the Applegate Valley. For additional insider tips follow @WinchesterInn on Twitter, as well as @Nancydbrown.

If You Go:
The Winchester Inn (800) 972-4991
35 South Second Street
Ashland, Oregon 97520

Article, photography and video by travel writer Nancy D. Brown. I was a guest of The Winchester Inn, however all opinions are my own.