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From296US$ /night
Check-in
24Feb2026Select date
Check-out
25Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

35 South 2Nd Street, Ashland, Oregon, United States, 97520
-
Close to Lithia Park
Perfect
9.4
9.7
/10
4.8
/5

Location

The Winchester Inn is situated just moments away from the Oregon Shakespeare Festival and the Oregon Cabaret Theater, positioning guests ideally to explore Ashland's cultural offerings. Visitors can easily access the town's local shops and galleries, enhancing their experience of Southern Oregon's charm. Surrounded by the scenic beauty of Ashland, outdoor adventures are just a short drive away.

Dining

On-site dining at the Winchester Inn includes the acclaimed Alchemy Restaurant and Bar, known for its craft cocktails and award-winning wine list. Guests can also enjoy the French-inspired steakhouse, Chateaubriand 36, which is located just across the street. Both establishments emphasize locally-sourced ingredients, providing a rich culinary experience.

Accommodations

The hotel offers 21 uniquely designed rooms and suites with distinct styles and luxurious touches. Each room includes Antica Farmacista toiletries, plush robes, and gourmet breakfast for two, ensuring comfort and convenience. Many accommodations also feature romantic fireplaces and picturesque views of the hills surrounding Ashland.

Amenities

Guests at the Winchester Inn can take advantage of complimentary evening turndown service and afternoon pastry treats delivered to their rooms. The property includes gardens with quiet sitting areas, creating spaces for relaxation. Valet service and same-day laundry are also available to enhance the overall guest experience.

Events

The Winchester Inn caters to both intimate gatherings and small corporate meetings, with spaces accommodating up to 30 participants. The hotel provides discreet service to meet event needs with catering options from its on-site restaurants. Planning assistance is available, ensuring successful events.

Highlights

Location: Steps from the Oregon Shakespeare Festival

Dining: Two acclaimed restaurants on-site

Accommodations: 21 uniquely designed rooms and suites

Services: Valet service and same-day laundry available

Must-do experiences

  • Catch a play at the Oregon Shakespeare Festival-truly iconic.
  • Savor the fresh, seasonal dishes at Larks Restaurant & Bar-delicious!
  • Visit the Ashland Saturday Market for local crafts and food vendors.
  • Stroll through Lithia Park for scenic views and lovely walking paths.
  • Explore the ScienceWorks Hands-On Museum for family-friendly fun.
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
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
Double Room Garden View
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
Standard Queen Room
2 persons
305 sq. feet 
1 King-size bed
Shower
Coffee machine
Queen Room
2 persons
360 sq. feet 
1 King-size bed
Shower
Coffee machine
Click button to see more rooms
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Price and Room Availability Calendar

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Facilities

Winchester Inn offers amenities for your comfortable stay and unforgettable experiences
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
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Dining Onsite

Winchester Inn boasts a delightful array of dining experiences, showcasing a blend of American, French, and local flavors in inviting settings. With options for every palate, guests can savor gourmet breakfasts, enjoy cozy dinners, and unwind with craft cocktails on the scenic outdoor patio.
Winchester Inn Ashland Restaurant photo The photo shows the interior of a stylish restaurant or bar. Large windows on the left side of the frame flood the space with natural light, offering a view of lush greenery outside. The room has a dark, sophisticated ambiance, with dark walls and a

Alchemy Restaurant and Bar

American and French with local and international influences
Ambiance
Modern and romantic, perfect for intimate dining or celebratory gatherings
Key Offerings
A thoughtfully curated menu featuring vegetarian, gluten-free, and dairy-free options, accompanied by a Best of Award of Excellence wine list and an exquisite cocktail selection.
Reservation
Recommended
Open Tuesday to Saturday from 4:00 PM to 9:00 PM

Chateaubriand 36

French steakhouse
Ambiance
Family-friendly, offering a warm and welcoming environment for both casual and special occasions
Key Offerings
Specializing in prime cuts of steak, complemented by classic French dishes, this restaurant promises a robust dining experience for all ages.
Reservation
Recommended
Open Wednesday to Saturday from 5:00 PM to 9:00 PM

Winchester Inn Location

35 South 2Nd Street, Ashland, Oregon, United States, 97520
Map view
35 South 2Nd Street, Ashland, Oregon, United States, 97520
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
Explore Ashland
Explore Ashland
Top Attractions
Activities
Dining
Entertainment
Oregon Shakespeare Festival
Oregon Shakespeare Festival
5 minutes' walk
Renowned theater venue showcasing world-class productions. A must-visit for arts lovers, offering performances year-round.
Lithia Park
Lithia Park
8 minutes' walk
Scenic park known for its tranquil ambiance, duck ponds, and walking paths. Ideal for picnics and leisurely strolls.
ScienceWorks Hands-On Museum
ScienceWorks Hands-On Museum
5 minutes' drive
Interactive science museum featuring engaging exhibits. Great for families, with programs and events for all ages.
Gathering Glass Studio
Gathering Glass Studio
9 minutes' walk
Glassblowing studio offering demonstrations and classes. Perfect for those interested in arts and crafts.
Hiking at Grizzly Peak Trail
10 minutes' drive
Thrilling hiking trail with stunning views. Ideal for outdoor enthusiasts looking for a challenging terrain.
Yoga at Ashland Yoga Center
7 minutes' walk
Relaxing yoga classes offered for all levels. A great way to unwind and rejuvenate during your stay.
Alchemy Restaurant and Bar
Alchemy Restaurant and Bar
1 minute' walk
Eclectic menu featuring local ingredients. Known for its vibrant atmosphere and creative cocktails.
Smithfields Restaurant and Bar
Smithfields Restaurant and Bar
1 minute' walk
Farm-to-table dining with a focus on local meats and produce. Cozy vibe, perfect for casual dinners.
Paddy Brannans Irish Pub
Paddy Brannans Irish Pub
1 minute' walk
Authentic Irish pub serving classic dishes and local brews. Great spot for a lively atmosphere and good times.
Ashland Independent Film Festival
5 minutes' walk (seasonal)
Annual film festival featuring independent films and screenings. A gathering place for film lovers each spring.
Glee Club Venue
5 minutes' walk
Live music venue showcasing local and touring acts. Family-friendly with diverse genres entertained throughout the week.
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
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
Cleanliness
9.6/10
Comfort
9.5/10
Facilities
9.4/10
Free Wi-Fi
9.1/10
Location
9.8/10
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.
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FAQs
About Winchester Inn
What is the check-in and check-out policy at Winchester Inn?
Check-in is from 16:00 and check-out is by 11:00.
How far is Winchester Inn from Rogue Valley International-Medford Airport?
The hotel is located 38 km from Rogue Valley International-Medford Airport.
What amenities are available in the rooms at Winchester Inn?
Rooms include air conditioning, a flat-screen TV, a refrigerator, a coffee maker, free Wi-Fi, and premium toiletries.
What dining options are available on-site at Winchester Inn?
Guests can enjoy an award-winning restaurant, Alchemy, which offers an à la carte, Full English/Irish, or American breakfast.
Are there restaurants nearby Winchester Inn?
Nearby restaurants include Larks Home Kitchen Cuisine, Hearsay Restaurant, NW Raw, and Pangea, all located within 0.5 km.
What recreational activities are available at Winchester Inn?
Guests can enjoy activities such as tennis, hiking, and access to local golf courses.
Does Winchester Inn have parking facilities?
The hotel offers free private parking on-site without the need for a reservation.
Is Wi-Fi available at Winchester Inn and is it complimentary?
Complimentary Wi-Fi is available throughout the property.
What unique features does Winchester Inn offer for guests?
The hotel features tiered English gardens, personalized service, and unique lodging options including cottages.
What entertainment options are nearby Winchester Inn?
The hotel is within walking distance of the Oregon Shakespeare Festival and numerous art galleries.
Does Winchester Inn have a bar or lounge area?
The hotel includes an on-site bar/lounge area where guests can enjoy a wide selection of beverages.

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