Winchester Inn Ashland Exterior photo This is a lovely, slightly whimsical photograph of a two-story house with a prominent porch. The house is painted a soft, creamy white with striking light blue trim around the windows, porch railings, and architectural details like the gable ends. 

Winchester Inn Ashland Exterior photo The photo shows a cozy, covered patio area, likely attached to a house, bathed in bright sunlight. The patio is paved with dark stones and features several seating arrangements. 

On the left side, a round metal table is surrounded by cushioned chairWinchester Inn Ashland Exterior photo The photograph shows a beautiful, multi-unit building, likely a hotel or guest house, on a sunny day. The building is a light blue with white trim and dark blue accents around the windows and rooflines. It has a classic architectural style with multi
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From220US$ /night
Check-in
19Apr2026Select date
Check-out
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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
4.9
4.6
/5

Dining

Winchester Inn is home to Alchemy Restaurant and Bar, where craft cocktails and an award-winning wine list featuring local Oregon products are available. Just across the street, Chateaubriand 36 brings French-inspired steakhouse dining to guests. Both dining options provide gourmet experiences just steps away from hotel accommodations.

Accommodations

The hotel offers 21 uniquely appointed rooms and suites, each blending classic design with contemporary amenities. Guest rooms include queen and king beds, private baths, and custom furnishings. Luxuries such as afternoon pastry treats and evening turndown service elevate the guest experience.

Location

Located just steps from the Oregon Shakespeare Festival, the hotel provides easy access to the arts and culture scene in Ashland. The nearby Oregon Cabaret Theater also offers an array of entertainment options. Guests can enjoy the scenic beauty of the Rogue Valley and surrounding hiking trails.

Additional Services

The hotel enhances the guest experience with twice-daily housekeeping and morning through evening valet service. Guests can opt for same-day laundry service and breakfast room service as well. Each room is stocked with Antica Farmacista toiletries and plush terry cloth robes for comfort.

Culinary Scene

The Winchester Inn serves as a gateway to Ashland's culinary landscape, offering a variety of dining options nearby. Guests can explore local farms and wineries, with over 150 wineries available in the Rogue Valley. The hotel is strategically placed for food lovers eager to discover regional delights.

Highlights

Dining: Alchemy Restaurant and Bar

Dining: Chateaubriand 36

Accommodations: queen and king beds

Accommodations: afternoon pastry treats

Location: Oregon Shakespeare Festival

Location: Oregon Cabaret Theater

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.
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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
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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
  • Wi-Fi
  • Free parking
  • Off-site car park
  • 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 (MFR)39 min  ·  16.0 mi
Klamath Falls (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 225 verified reviews
9.4/10
Perfect
95%
Recommend
Cleanliness
9.5/10
Comfort
9.6/10
Facilities
9.4/10
Free Wi-Fi
9.7/10
Location
9.8/10
Staff
9.6/10
Value for money
9.2/10
Guest reviews
based on 430 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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Check-in
19Apr2026Select date
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Rooms and Guests2 Guests, 1 Room