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United States
Ashland
Winchester Inn
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Winchester Inn, Ashland

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Up to 10% cheaper
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Check rooms and rates
From296US$ /night
Check-in
26Feb2026Select date
Check-out
27Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

35 South 2Nd Street, Ashland, Oregon, United States, 97520
Perfect
9.4
9.7
/10
4.8
/5
“The hotel is perfectly situated just two blocks from the Shakespeare Festival, making it easy to enjoy the local culture.”view full review

The Winchester Inn, a 5-star hotel, offers luxury and comfort with convenient access to art galleries and the Oregon Shakespeare Festival. This acclaimed Ashland hotel features fine dining at Alchemy Restaurant and Bar, award-winning for its wine and cocktail program.

Rooms & Amenities

Winchester Inn provides a range of lodging options, including luxurious rooms, suites, and cottages. Every accommodation features amenities such as flat-screen TVs, Antica Farmacista toiletries, and gourmet breakfast for two.

Dining & Options

Dining includes the celebrated Alchemy Restaurant, recognized for its innovative cuisine using seasonal ingredients, and a sophisticated wine list. Guests can also enjoy afternoon pastry treats delivered to their rooms.

Leisure & Activities

Guests can relax in the award-winning gardens featuring small sitting areas, perfect for reading or enjoying a glass of wine. The Winchester Inn is also a short distance from the Oregon Shakespeare Festival and local wineries, offering various cultural experiences.

Services & Business

The Winchester Inn provides attentive service, including valet parking, laundry service, and morning coffee. For business events, the hotel offers meeting facilities that can accommodate up to 30 participants.

View all

Select your room type

Winchester Inn offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Comfort Triple Room Shower
Comfort Triple Room Shower
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Double Room Garden View
Double Room Garden View
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Standard Queen Room
Standard Queen Room
2 persons
305 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Queen Room
Queen Room
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
room details
Click button to see more rooms
Show all rooms
Show all roomsLess

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

Winchester Inn offers amenities for your comfortable stay and unforgettable experiences
Delicious Breakfast!
“The breakfast was a standout feature, with a great variety of high-quality food served in a lovely atmosphere.” view full review
Comfortable Rooms!
“The rooms were incredibly comfortable, with amazing bedding and all the little extras like a stocked fridge that made our stay special.” view full review
Luxury Showers!
“The showers were a perfect blend of luxury and functionality, complete with plush bathrobes that added to the relaxing experience.” view full review
Tasty Treats!
“The complimentary snacks, especially the gluten-free cookies, were a good bonus that made our stay even sweeter!” view full review
Facilities: Perfect
9.4/10Review score

General

  • No smoking on site
  • Free 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
Show more

Winchester Inn Location

35 South 2Nd Street, Ashland, Oregon, United States, 97520
Map view
35 South 2Nd Street, Ashland, Oregon, United States, 97520
City landmarks
Park
Lithia Park
2100 ft
Museum
ScienceWorks Hands-On Museum
1.4 mi
Landmark
Gathering Glass Studio
2200 ft
Museum
Schneider Museum of Art
1.2 mi
Park
North Mountain Park
1.3 mi
Landmark
Railroad Park
3600 ft
Landmark
Oakleaf Studio
2200 ft
Gallery
Ashland Art Works
2400 ft
Landmark
Garfield Park
4900 ft
Landmark
Ashland Creek Park
3600 ft
Landmark
Illahe Studios and Gallery
3700 ft
Landmark
Ashland Creek
4700 ft
Landmark
The Siskiyou
1.0 mi
Landmark
Ashland Dog Park
1.3 mi
Landmark
Acid Castle Boulders Access Point
1.2 mi
Landmark
North Mountain Park Nature Center
1.3 mi
Landmark
Hald/ Strawberry Park
1.4 mi
Landmark
Hunter Park
1.5 mi
Store
Deja Vu
1.5 mi
Nearby
Theatre
Oregon Shakespeare Festival
1300 ft
Library
Ashland Library
900 ft
Library
Ashland
1000 ft
111 E Main St
Zagorska Oasis
1200 ft
Store
Ashland Food Co-op
1800 ft
Park
Bluebird Park
1900 ft
264 E Main St
Prize
500 ft
Gallery
Ashland Art Center
600 ft
N Main St
Lithia Fountains
1600 ft
Store
Northwest Nature Shop
1800 ft
N Main St
Downtown Plaza
1800 ft
Restaurants
Alchemy Restaurant and Bar
100 ft
35 S 2nd St at the Winchester Inn
Smithfields Restaurant and Bar
200 ft
36 South 2nd Street
Paddy Brannans Irish Pub
200 ft
23 S 2nd St
Pangea
400 ft
272 E Main St
Hearsay Restaurant
400 ft
40 S 1st St
Cafe Aroma & AromaDome Wellness Center
300 ft
296 E Main St
Pie + Vine
500 ft
358 East Main Street
Redzone Sports Bar N Grill
400 ft
303 E Main St
The Village Baker of Ashland
600 ft
372 E Main St
Getting around
City Centre
Ashland4 min  ·  1000 ft
Airports
Rogue Valley International-Medford Airport (MFR)39 min  ·  16.0 mi
Klamath Falls Airport (LMT)158 min  ·  65.4 mi
Bus
Bus stop3 min  ·  700 ft
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Property information and rules
Check-in
from 16:00-23:59
Check-out
until 11 am
Guest Parking
Private parking is possible on site for free.
Internet
Wireless internet is available in for free.
Breakfast
At the hotel Winchester Inn guests are invited to a full breakfast served for free. 
Pets
Pets are not allowed.
Number of rooms:
21

Reviews and Ratings

Feedback about Winchester Inn from previous guests about their experience.
Review score
Based on 204 verified reviews
9.4/10
Perfect
96%
Recommend
Breakfast
8.5/10
Cleanliness
9.6/10
Comfort
9.5/10
Facilities
9.4/10
Free Wi-Fi
9.1/10
Location
9.8/10
Paid Wi-Fi
9.9/10
Staff
9.7/10
Value for money
9.2/10
Guest reviews
based on 415 reviews
9.4/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews

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Check-in
26Feb2026Select date
Check-out
27Feb2026Select date
Rooms and Guests2 Guests, 1 Room
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  • Price calendar
  • Facilities
  • Location
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