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The Winchester Inn, Ashland, OR
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The Winchester Inn

The Winchester Inn is a place to stay in Ashland, OR, part of the Southern Oregon guide. Cost: $50 or more.

35 South Second Street · Ashland, OR

Why you should go…

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

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.

    Right next doorSwitch it up: Eat & Drink

  • Shopping
    Local Gem

    True Lavender Collective

    Free

    Downtown Ashland boutique selling lavender candles, oils and gifts sourced from Oregon farms.

    Right next doorSwitch it up: Shopping

  • Theatre & Events
    Iconic

    Oregon Shakespeare Festival

    $25–$50

    Repertory theatre festival in Ashland, Oregon staging classic and contemporary plays across three stages each season.

    Right next doorSwitch it up: Theatre & Events

  • Stay
    Date Night

    Weasku Inn

    $50+

    Historic riverfront inn on the Rogue River near Grants Pass with lodge rooms and private cabins.

    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
    Iconic

    Seven Feathers Casino Resort

    Free

    Tribal casino resort in Canyonville, Oregon with over 900 slots, table games, a spa, and an RV park.

    59 mi awayMore like this

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