Skip to main content.
All properties in Ashland, Oregon, United States of America
1 room, 2 adults

Winchester Inn, Ashland

3.5-star3.5 stars
35 S. 2nd St., Ashland, OR, 97520, United States of America

Victorian inn in Historic Downtown District with restaurant, bar/lounge
  • Free cooked-to-order breakfast, free WiFi, and free parking
  • Collect nightsYou can collect® Rewards nights here
  • Price Guarantee
From 273 reviews. TripAdvisor Traveler Rating.

TripAdvisor Traveller Rating

Great location
Awesome vibe
Delicious food
Great room

Winchester Inn, Ashland

from $235
  • Double Room, 1 Bedroom (Garden)
  • Double Room, 1 Bedroom (Sylvan)
  • Double Room (Queen Anne)
  • Double Room, 1 Queen Bed (Patio)
  • Double Room, 1 Queen Bed (Marjorie Roy)
  • Double Room, 1 Queen Bed (Catharine M)
  • Double Room, 1 King Bed (Sunset)
  • Double Room, 1 King Bed (Andrew G)
  • Double Room, 1 King Bed (Peter Benjamin)
  • Double Room, 1 King Bed (Eastlake)
  • Double Room, 1 King Bed (Enders)
  • Suite, 1 King Bed with Sofa bed (Robert Gordon)
  • Suite, 2 Bedrooms (Duet Suite)
  • Suite, 1 King Bed (Hargadine)
  • Suite, 1 King Bed (Barbara Howard)
  • Suite, 1 King Bed (Eleanor Rose)
  • Suite, 1 Bedroom (Silverdale)
  • Suite, 1 Queen Bed with Sofa bed (Brighton)
  • Suite, 1 Queen Bed with Sofa bed (Belvedere)
  • Suite, 1 Queen Bed with Sofa bed (Courtyard)
  • Suite, 1 King Bed (Fordyce)
  • Studio Suite, 1 Queen Bed, Kitchenette
  • Suite, 1 King Bed, Kitchenette
  • Family Suite, 2 Bedrooms, Kitchenette, City View

What’s around Winchester Inn, Ashland


  • In Historic Downtown District
  • Oregon Cabaret Theatre - 2 min walk
  • Ashland Library - 3 min walk
  • Thomas Theatre - 4 min walk
  • Angus Bowmer Theatre - 5 min walk
  • Allen Elizabethan Theatre - 5 min walk
  • Lithia Park - 16 min walk
  • Southern Oregon University - 21 min walk

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 22 min drive

At a glance

Key facts


  • 21 rooms
  • Arranged over 3 floors


  • Check-in time 3 PM-9 PM
  • Check-out time is 11 AM
The front desk is open daily from 7:30 AM - 8 PM.
The check-in location differs from the property location. To check in, go to The check-in is at Winchester Inn for both properties
If you are planning to arrive after 9 PM please contact the property in advance using the information on the booking confirmation. Check-in is at 3 PM. Guests planning to arrive after hours must contact the bed and breakfast at least 48 hours prior to arrival to receive late check-in instructions.

Guests can contact the office using the number on the reservation confirmation received after booking via this Web site.

Required at check-in

  • Credit card or cash deposit required

  • Government-issued photo ID required

  • Minimum check-in age is 21

Travelling with others


  • No cribs (infant beds)


  • Pets not allowed


  • Free WiFi in public areas

  • Free WiFi in rooms



  • Free self parking

Payment types at the property

Other information

  • Smoke-free property
* See small print for additional details or extra charges

At the property

Food and drink
  • Free cooked-to-order breakfast daily
  • Restaurant
  • Bar/lounge
Working away
  • One meeting room 1
  • Front desk (limited hours)
  • Concierge services
  • Tours/ticket assistance
  • Free newspapers in lobby
  • Luggage storage
  • Number of buildings/towers - 5
  • Year Built - 1886
  • Garden
  • Terrace
  • Accessible bathroom
  • In-room accessibility
  • Roll-in shower
Languages Spoken
  • English

In the room

Home comforts
  • Air conditioning
  • Coffee/tea maker
  • Bathrobes
  • Iron/ironing board
Sleep well
  • Hypo-allergenic bedding available
  • Down comforter
  • Turndown service
  • Premium bedding
  • Pillowtop mattress
Things to enjoy
  • Individually decorated
  • Individually furnished
Freshen up
  • Designer toiletries
  • Hair dryer
Be entertained
  • Flat-screen TV
  • Cable TV channels
Stay connected
  • Free WiFi
  • Phone
  • Daily housekeeping

Winchester Inn, Ashland’s small print

Also known as

  • Winchester Inn Ashland
  • Winchester Ashland
  • The Winchester Inn


Only registered guests are allowed in the guestrooms.

This property does not have elevators.

Please note that cultural norms and guest policies may differ by country and by property. The policies listed are provided by the property.

Mandatory fees

You’ll be asked to pay the following charges at check in or check out:

  • City/local tax: USD 9.0

We have included all charges provided to us by this property. However, charges can vary, for example, based on length of stay or the unit you book.

Didn’t find the right property?

Continue searching for Ashland, Oregon, United States of America

Recent reviews

Exceptional 9.6 From 61 reviews

Exceptional 10.0
Stop here , you'll love it!
Fabulous stop over on a trip to/from Portland
David, us1 night romance trip
Exceptional 10.0
happy repeaters
We try to stay here 2 or three times a year, because it is just comfortable in a great location and the breakfast included is so good.
Paul, us1 night romance trip
Exceptional 10.0
Overall review
Very cute room! Fresh danishes in room that were tasty. Very clean. Refrigerator,tea and creamers available. Large bathtub with lovely toiletries. Bathrobes were very comfortable. Nice Happy Hour. The hot breakfast was made to order and tasted very good. Large variety of other restaurants,shops,breweries and wineries close by. Priced very well! So glad that we made the trip and stayed at Winchester Inn.
us1 night romance trip
Very Good 8.0
Beautiful B&B in great location
Friendly staff, loved having a restaurant/bar at the property, and very walkable location. Our room was gorgeous, but you definitely realize that you are in part of a house as far as noise/privacy. Don't make the mistake we did when we turned down housekeeping shortly after checking in; we assumed it was a turn-down service, but we in fact missed the pastry/dessert they bring.
Katherine, us1 night romance trip
Very Good 8.0
We had an amazing time. From the kind and helpful staff to their food and bar, we were never left needing anything.
Natalie, us1 night romance trip

Winchester Inn, Ashland

Is the description of this hotel not correct? Tell us