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Winchester Inn

4.6(216)
Hotel

About

The Winchester Inn blends Victorian charm with modern luxury in downtown Ashland, offering uniquely furnished rooms with plush beds and spa-like bathrooms. Its rich history as a private home and hospital adds character to a refined lodging experience steps from the Oregon Shakespeare Festival.

Onsite dining includes Alchemy Restaurant and Bar, known for craft cocktails and an award-winning Oregon wine list, plus nearby Chateaubriand 36 for upscale French-inspired steakhouse fare. The Inn’s attentive service and gourmet breakfast make it a distinguished choice for business travelers and cultural visitors alike.

Best for

  • Executive retreats & boutique lodging
  • Client dinners with refined dining
  • Cultural event stays near theaters

Request a Package

Tell the venue what you're planning and they'll respond with a custom proposal within 1–2 business days.

Group Meeting

Custom request

Professional meeting space for your team — whether it's a meeting, training, workshop, or multi-day offsite. Half-day, full-day, or multi-day — with the option to request AV, catering, and your preferred room layout.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology

Room Block

Custom request

Reserve a block of rooms for your group — ideal for multi-day conferences, offsites, or any event where attendees are traveling from out of town.

What's typically included

  • Reserved guest rooms for your group
  • Flexible check-in & check-out dates
  • Negotiated group rates

Meeting + Room Block

Custom request

Bundle your meeting space and guest rooms in one request — perfect for multi-day offsites and conferences where the team meets by day and stays overnight.

What's typically included

  • Meeting room & layout
  • Food & beverage
  • AV & technology
  • Reserved guest rooms for your group

Venue Details

Standout features

Victorian architecture with a rich past
History
Victorian architecture with a rich past
Originally built in 1886 as a private home, the building showcases authentic Victorian charm and has served as a hospital and apartment complex before becoming a boutique hotel.
Downtown Ashland near cultural landmarks
Location
Downtown Ashland near cultural landmarks
Situated steps away from the Oregon Shakespeare Festival and close to the Oregon Cabaret Theater, the inn offers easy access to Ashland’s vibrant arts and culture scene.
Luxurious room details and gourmet breakfast
Amenities
Luxurious room details and gourmet breakfast
Rooms feature 600 thread count sateen sheets, Antica Farmacista toiletries, and spa-like bathrooms, complemented by a complimentary 2-course gourmet breakfast.

At a glance

Rated 4.6 on Google · 216 reviews