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The Winchester Inn

Victorian boutique inn from 1886 in downtown Ashland, two blocks from the Oregon Shakespeare Festival, with gardens and the on-site Alchemy Restaurant and Bar.

35 South Second Street · Ashland, OR

About The Winchester Inn

The Winchester Inn occupies an 1886 Victorian residence in downtown Ashland that has also served as the Southern Oregon Hospital before becoming a boutique hotel in 1983. Its 11 rooms and 9 suites sit among English-style gardens two blocks from the Oregon Shakespeare Festival theatres. Rates include a two-course breakfast and afternoon pastries, and the on-site Alchemy Restaurant and Bar serves dinner with an Oregon-focused wine list; sister steakhouse Chateaubriand 36 is across the street.

#inn
#victorian
#ashland
#shakespeare festival
#fine dining

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What's around here?

The closest stops to The Winchester Inn, ordered by straight-line distance. A few more like it, plus some different kinds of fun so you can build a full day.

Eat & Drink
Date Night
Belle Fiore Winery
Under $25
Estate winery near Ashland offering wine tastings, a wine bar, vineyard tours and fine dining.
Transit: reachable by public transit
Right next doorSwitch it up: Eat & Drink
Shopping
Local Gem
True Lavender Collective
No admission fee
Downtown Ashland boutique selling lavender candles, oils and gifts sourced from Oregon farms.
Transit: reachable by public transit
Right next doorSwitch it up: Shopping
Theater & Events
Iconic
Oregon Shakespeare Festival
$25–$50
Repertory theatre festival in Ashland, Oregon staging classic and contemporary plays across three stages each season.
Transit: reachable by public transit
Right next doorSwitch it up: Theater & Events
Stay
Date Night
Weasku Inn
$50+
Historic riverfront inn on the Rogue River near Grants Pass with lodge rooms and private cabins.
Transit: reachable by public transit
33 mi awayMore like this
Stay
Outdoor Adventure
Union Creek Resort
$50+
A rustic cabin resort on the Rogue River near Crater Lake, with historic cabins, a cafe and access to hiking and winter trails.
51 mi awayMore like this
Stay
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Seven Feathers Casino Resort
No admission fee
Tribal casino resort in Canyonville, Oregon with over 900 slots, table games, a spa, and an RV park.
59 mi awayMore like this