Winchester Inn, Ashland

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From455US$ /night
Check-in
08Aug2025Select date
Check-out
09Aug2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

35 S. 2Nd St., Ashland, Oregon, United States, 97520

The Winchester Inn, a 5-star landmark in Ashland for over 30 years, features 21 rooms across a property with tiered English gardens and holds Wine Spectator's Best of Award of Excellence, recently named one of America's Great Bourbon Bars.

Luxury Room Amenities

Each Winchester Inn guestroom features premium bedding, air conditioning, imported Antica Farmacista toiletries, and bathrobes, with select rooms offering fireplaces and hill views. Every suite includes marble-tiled showers and extra living space, while cottages provide private entrances ideal for families seeking shared accommodation with privacy.

Distinguished Dining Experience

The Winchester's Alchemy Restaurant and Bar delivers critically acclaimed dining with an award-winning wine program. Guests receive a complimentary 2-course gourmet breakfast, with afternoon pastry service delivered to rooms.

Garden and Services

The property features multiple garden sitting areas for quiet relaxation. The hotel maintains high cleanliness standards with twice-daily housekeeping service and offers same-day laundry service.

Theater District Location

Located blocks from the Tony Award-winning Oregon Shakespeare Festival, presenting eight months of performances annually. The hotel sits 18.5 miles from Rogue Valley International-Medford airport, with nearby access to over 150 regional wineries.

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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Comfort Triple Room Shower
Max:
2 persons
33 m² 
Bed options:
1 King-size bed
Garden view
Shower
Coffee machine
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Double Room Garden View
Max:
2 persons
33 m² 
Bed options:
1 King-size bed
Garden view
Shower
Coffee machine
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Standard Queen Room
Max:
2 persons
28 m² 
Bed options:
1 King-size bed
Garden view
Shower
Coffee machine
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Getting around

A guide to all available transportation options

City Centre
Ashland300 m
Airports
Rogue Valley International-Medford (MFR) 25.7 km
Klamath Falls (LMT) 105.2 km
Bus
Bus stop200 m

Facilities

Experience a variety of amenities at the boutique hotel, crafted to ensure your comfort and unforgettable moments

General

  • No smoking on site
  • Wi-Fi
  • Parking
  • Concierge desk
  • No pets allowed
  • Rooms/ Facilities for disabled
  • Luggage storage
  • Allergy-free rooms
  • Smoke detectors
  • Fire extinguishers
  • Key access

Sports & Fitness

  • Hiking
  • Tennis court
  • Golf course

Guest Parking

  • Electric kettle

Services

  • Housekeeping
  • Dry cleaning
  • Welcome drink
  • Happy hour

Dining

  • Restaurant
  • Bar/ Lounge area
  • Dinner
  • Special diet menus

Business

  • Meeting/ Banquet facilities
  • Fax/Photocopying

Children

  • Cots

Spa & Leisure

  • Garden area

Room features

  • Air conditioning
  • Heating
  • Mini-bar
  • Sitting area
  • Patio
  • Garden furniture
  • Tea and coffee facilities
  • Ironing facilities

Bathroom

  • Free toiletries

Self-catering

  • Electric kettle

Media

  • Flat-screen TV
  • AM/FM alarm clock

Room decor

  • Carpeted floor
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Location

35 S. 2Nd St., Ashland, Oregon, United States, 97520
Map view
35 S. 2Nd St., Ashland, Oregon, United States, 97520
Nearby
Theatre
Oregon Shakespeare Festival
390 m
Library
Ashland Library
250 m
Library
Ashland
300 m
111 E Main St
Zagorska Oasis
340 m
Store
Ashland Food Co-op
530 m
Park
Bluebird Park
550 m
264 E Main St
Prize
140 m
Gallery
Ashland Art Center
170 m
N Main St
Lithia Fountains
470 m
Store
Northwest Nature Shop
520 m
N Main St
Downtown Plaza
540 m
Restaurants
Alchemy Restaurant and Bar
10 m
35 S 2nd St at the Winchester Inn
Smithfields Restaurant and Bar
50 m
36 South 2nd Street
Paddy Brannans Irish Pub
50 m
23 S 2nd St
Pangea
110 m
272 E Main St
Hearsay Restaurant
120 m
40 S 1st St
Cafe Aroma & AromaDome Wellness Center
90 m
296 E Main St
Pie + Vine
130 m
358 East Main Street
Redzone Sports Bar N Grill
100 m
303 E Main St
The Village Baker of Ashland
160 m
372 E Main St
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Check-in
08Aug2025Select date
Check-out
09Aug2025Select date
Rooms and Guests2 Guests, 1 Room