Winchester Inn      
35 S 2nd St, Ashland, OR 97520-2877, USA    
(800) 972-4991, (541) 488-1113


  1. Winchester Inn, Ashland Oregon...
  2. Sunset Room...
  3. Fordyce Suite...
  4. Sylvan Room...
  5. Catharine M Room...

- $325

Book a Room $195 - $325

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Circa 1886. Gracing downtown Ashland, only two blocks from the Oregon Shakespeare Festival, this boutique inn offers much more than just a great location. The award-winning restaurant and wine bar enhance every stay along with the luxurious surroundings and generous amenities. Relax in the gazebo amid the English-tiered gardens. Inviting guest rooms and suites include bath robes, Egyptian cotton towels, turndown service and afternoon pastry treats. Some boast a two-person jetted tub and fireplace. Linger over a hearty two-course gourmet breakfast with three entrée selections to enjoy in the dining room or on the outdoor patio. A seasonal dinner menu is also available. Ask about special services and packages. Weddings are popular events amid this gorgeous setting.

For more information visit the website.


$195 to $325

Off Season: $95 to $195

Payment Types Accepted Include American Express, Discover, Master Card, Personal Checks, Travelers Checks, Visa and Cash.

    • Snacks/Refreshments
    • Breakfast


This property has 6 total guest accommodations, 19 with private bath, 7 with fireplaces, 6 with whirlpools, 8 total suites, including 4 two-bedroom suites, 2 cottages and 1 conference room.

  • Air Conditioning
  • Bath Amenities
  • Bathrobes
  • Cable TV
  • Coffeemaker
  • Copy Machine
  • Fax
  • Fireplace
  • Gift Shop
  • Hair Dryer
  • Iron/Ironing Board
  • Refrigerator
  • Telephone
  • Television
  • Turn-Down Service
  • Wireless Internet Access

Business Traveler Amenities

  • Gym Nearby
  • Off-site Dry Cleaning Services
  • Television
  • Wireless Internet Access

Events Hosted

    • Honeymoons
    • Meetings
    • Family Reunions
    • Romantic Getaways
    • Weddings
    • Retreats

Spa Services

Off-Site Spa Services Available

Nearby Recommended Spas

Blue Giraffe Spa
(541) 488-3335

Waterstone Spa
(541) 488-0325

Liquor License

    • Full

Romantic Interest

Three Course Dinner for Two - $80 Enjoy a three course Prix Fixe meal in our romantic award-winning restaurant. Includes your choice of appetizers, soup or salad, and entree. Seasonal Bouquet of Flowers - $55 LG/ $35 Sm Your choice of a large or small bouquet waiting for you in the room. A Dozen Roses - Market Price Enjoy a dozen roses decorating your room. Color and availablity are subject to season. Please call to arrange. Half a Dozen House Made Truffles - $14

Innkeepers Association Memberships

Unique Inns

Describe Garden and Grounds

We are surrounded by English tiered gardens and large oak trees.

Reservation/Cancellation Policies:


Prepayments are refunded ONLY if notice of cancellation is received 30 days prior to the scheduled date of arrival. Right reserved to withhold the entire prepayment if less than 30 days is given. A 20% cancellation fee will be withheld from a prepayment for partial or complete cancellations. A 20% fee will be deducted for date changes.


Outside Only.

Other Activities

    • Antiquing
    • Art Galleries
    • Bicycling
    • Canoeing/Kayaking
    • Fishing
    • Golf
    • Hiking
    • Live Theater
    • Museums
    • Parks
    • Shopping (Local Crafts)
    • Skiing Cross Country
    • Skiing Downhill
    • Tennis
    • Water Sports
    • Wineries

Historic Interest

The building was used as the first southern Oregon Hospital.

Historic Awards:

  • City Historical Site (Applied)
  • National Historical Site (Applied)
  • State Historical Site (Applied)

Other Awards:

Wine Spectator Award of Excellence 2006-2010

Nearby College/University

Southern Oregon University

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Other Ratings: "3 AAA Diamonds, ""3 Mobil Stars, "iLoveInns Guests

Publicity and Press Reviews

"...The Winchester is Ashland's premier historic inn."
The New York Times

2006, 2007, 2008, 2009, 2010, 2011
Wine Spectator Award of Excellence

"The West's Best Small Inns"
Sunset Magazine.


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