"Charming and comfortable. A wonderful staff and among the best breakfasts I ever had"
Daniel from United States
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"Beautiful property, charming room, great location, tasty made-to-order (not a buffet!) breakfast."
Bridget from United States
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"Everything was clean, comfortable, and fit the vibe of Ashland."
Beth from United States
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"The complementary breakfast was absolutely delicious, staff were wonderful & the Inn & garden were charming."
Danielle B from United States
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"What wonderful, warm, professional service! The staff really made an effort to make us feel welcome and to meet our needs."
Owen M from United States
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4-star boutique hotel in Ashland with historic charm and onsite restaurant
Accommodations
The Winchester Inn offers 18 individually decorated rooms, each equipped with distinctive furnishings and artwork. Guests can choose from various types, including queen and king rooms, providing a blend of comfort and style. Cozy sitting areas are included, enhancing the overall convenience for visitors.
Dining
The Inn features a farm-to-table restaurant called the Winchester Inn Restaurant, known for its seasonal menu crafted from locally sourced ingredients. The restaurant provides an intimate setting for breakfast, lunch, and dinner, highlighting the culinary talents of the staff. Additionally, guests can enjoy wine from the extensive wine list, showcasing local and international selections.
Location
Situated in Ashland, the hotel is conveniently located near the renowned Oregon Shakespeare Festival. Guests can explore the surrounding area, including local shops, art galleries, and coffee houses, all within walking distance. The peaceful setting allows visitors to appreciate the beauty of the nearby mountains and parks.
Outdoor Space
The Winchester Inn features beautifully landscaped gardens and outdoor seating areas, ideal for relaxation and socializing. Guests have access to private patios and balconies that provide picturesque views of the surrounding landscape. Outdoor fire pits add additional charm to the ambiance during cooler evenings.
Events and Activities
The hotel specializes in hosting intimate events, from weddings to corporate gatherings, with personalized planning services available. Guests can take advantage of nearby hiking trails and cycling routes for outdoor adventures. Local cultural events and festivals further immerse visitors in Ashland's vibrant community.
Highlights
Accommodations: 18 individually decorated rooms
Dining: Winchester Inn Restaurant with seasonal menu
Location: Near Oregon Shakespeare Festival
Outdoor Space: Beautifully landscaped gardens
“Winchester Inn truly understands hospitality, blending professional service with genuinely thoughtful touches that make you feel welcomed the moment you arrive. Its charming atmosphere, amplified by beautiful grounds and exceptionally comfortable rooms, is matched by a spectacular, multi-course breakfast that sets a refined tone for the day. The inn's prime location simply solidifies its appeal, placing you right at the heart of Ashland's attractions.”
James DavidEditor-in-Chief at Usoregon
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
33 sq. feet
1 King-size bed
Air conditioning
Heating
room details
Double Room Garden View
2 persons
33 sq. feet
1 King-size bed
Air conditioning
Heating
room details
Standard Queen Room
2 persons
28 sq. feet
1 King-size bed
Air conditioning
Balcony
room details
Show all rooms
Price and Room Availability Calendar
Check availability and prices for your dates now!
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Check-in/ Check-out
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
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
Dining Onsite
At Winchester Inn, guests are invited to savor a culinary experience that beautifully blends local and international flavors. With two distinct dining venues, each offers a unique ambiance and a commitment to elevating every meal with creativity and attention to detail.
Alchemy Restaurant and Bar
American, French, Local, International
Ambiance
Modern, Romantic
Key Offerings
Signature dishes crafted for both food lovers and health-conscious diners, along with an award-winning wine and cocktail selection that has earned accolades for its excellence.
Reservation
Recommended for peak dining times
Open 5:00 PM until close
Chateaubriand 36
French, Steakhouse
Ambiance
Family-friendly
Key Offerings
A diverse menu featuring classic French dishes and expertly prepared steaks, perfect for a cozy family dinner.
Reservation
Recommended for dinner service
Open for dinner
Winchester Inn Location
35 South 2Nd Street, Ashland, 97520,
Explore Ashland
Explore Ashland
Top Attractions
Activities
Dining
Entertainment
Oregon Shakespeare Festival
5 minutes' walk
Renowned for its world-class theater productions, this festival showcases performances across multiple stages year-round.
Lithia Park
8 minutes' walk
A stunning park offering beautiful gardens, walking paths, and a serene atmosphere perfect for a leisurely stroll.
ScienceWorks Hands-On Museum
25 minutes walking
Interactive exhibits focused on science and technology, providing engaging activities for all ages. Ideal for families.
Schneider Museum of Art
25 minutes walking
Features contemporary art from local and international artists, hosting rotating exhibitions and educational programs.
Grizzly Peak Trail
25 minutes driving
A challenging hike with breathtaking views of the Rogue Valley, perfect for thrill-seekers eager to explore nature.
Yoga Classes at Ashland Yoga
5 minutes' walk
Relaxing yoga sessions offered in a tranquil setting, catering to all skill levels with drop-in classes available.
Alchemy Restaurant and Bar
1 minute' walk
Innovative farm-to-table cuisine with a cozy atmosphere. Try their seasonal dishes and extensive wine selection.
Smithfields Restaurant and Bar
1 minute' walk
Upscale bar and grill featuring local meats and craft spirits in a laid-back yet elegant setting, perfect for dinner.
The Black Swan Theater
5 minutes' walk
Offers a vibrant lineup of performances, including plays and musicals, creating a lively nightlife atmosphere.
Ashland Community Center
4 minutes' walk
Hosts family-friendly events, including movie nights and arts festivals, fostering community spirit among guests.
Getting around
City Centre
Ashland 4 min · 1000 ft
Airports
Rogue Valley International-Medford (MFR) 39 min · 16.0 mi
Klamath Falls (LMT) 158 min · 65.4 mi
Bus
Bus stop 3 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 the entire hotel 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:
23
Reviews and Ratings
Feedback about Winchester Inn from previous guests about their experience.
Review score
Based on 266 verified reviews
9.3 /10
Perfect
95 %
Recommend
Cleanliness
9.5/10
Comfort
9.6/10
Facilities
9.4/10
Free WiFi
9.8/10
Location
9.8/10
Staff
9.6/10
Value for money
9.2/10
Pros
Gourmet breakfast
Comfortable beds
Cute staff
House-baked cookies
Cons
Undisclosed fees
Musty room smell
Guest reviews
based on 426 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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