Skip to content
BusinessesGrow
StayHistoricFoodie PickLocal Favorite

The Winchester Inn

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

Good to know

General stay guidance

Habits that pay off across this whole category, not rules for this one venue. Always check the official site for the specifics.

  • Rates swing with the calendar

    Midweek nights and shoulder-season dates are usually the kindest on price.

  • Read what is included

    Parking, resort fees, and breakfast are the three extras that most often land on the final bill.

  • Ask at booking, not at the desk

    Early check-in, late checkout, and room preferences go further when you request them in advance.

  • On a short trip, location wins

    What you can reach on foot from the door matters more than the amenities list.

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