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From296US$ /night
Check-in
19Jan2026Select date
Check-out
20Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

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

Rooms and Suites

The Winchester Inn provides 21 rooms, suites, and cottages. Rooms have queen or king beds and private bathrooms. All rooms include flat-screen TVs, honor bars, Antica Farmacista toiletries, robes, and gourmet breakfast for two. Suites feature soaking tubs, jacuzzi baths, or marble-tiled showers. Cottages include private entrances and are suitable for families.

Dining at Winchester

Alchemy Restaurant and Bar is located in the Winchester Inn. It is critically acclaimed for its kitchen, wine, and cocktail program. The wine list has a Best of Award of Excellence from the Wine Spectator. Alchemy is open from 5:00 PM until closing time. The bar opens at 4:00 PM. Chateaubriand 36, a French-inspired steakhouse, is located across the street.

Things to Do

Guests can explore the gardens with sitting areas. The Oregon Shakespeare Festival, one of the oldest non-profit theaters in the nation, is near the Winchester Inn and presents plays, backstage tours, and educational programs. Paschal Winery and StoneRiver Vineyards are also nearby.

Location and Access

The Winchester Inn is located in Ashland, Oregon, near the Oregon Shakespeare Festival and the Oregon Cabaret Theater. Lithia Park is 0.5 km away. Gathering Glass Studio, Downtown Plaza, Ashland Food Co-op and Lithia Fountains are also 0.5 km away. Rogue Valley International-Medford Airport is 30 km from the inn.

Hotel Services

Winchester Inn guest rooms include fresh flowers and afternoon pastry treats. Amenities include free WiFi, free parking, and a 2-course gourmet breakfast. Additional services include valet service, same-day laundry service, and room service for breakfast. Housekeeping services rooms twice daily. High-speed wireless internet is accessible throughout the property.

“I believe what sets this inn apart is its blend of historic charm and modern luxury, particularly evident in the well-appointed rooms and award-winning Alchemy Restaurant. Its location is ideal for those attending the Oregon Shakespeare Festival or wishing to explore downtown Ashland. For those reasons, I see it as more than just a place to stay; it's a destination in itself.”
Hotel logo
James DavidEditor-in-Chief at Tohotel
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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
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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Price and Room Availability Calendar

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Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free 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

At Winchester Inn, guests are invited to indulge in a delightful array of dining options that celebrate both local and international flavors. With a focus on quality and inviting atmospheres, these culinary experiences promise to satisfy any palate while providing a charming backdrop for meals.
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, French, Local, International
Ambiance
Modern, Romantic
Key Offerings
Features a highly rated wine and cocktail program, including award-winning selections, with a charming outdoor patio for al fresco dining. A two-course gourmet breakfast is provided at no additional cost.
Reservation
Recommended
Tuesday to Saturday, 4:00 PM - 9:00 PM

Chateaubriand 36

French, Steakhouse
Ambiance
Family friendly
Key Offerings
Known for its classic French and steakhouse dishes in a welcoming environment, perfect for family gatherings or special occasions.
Reservation
Recommended
Wednesday to Saturday, 5:00 PM - 9:00 PM

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 festival showcasing classic and contemporary performances. Unique experience for theater enthusiasts.
Lithia Park
Lithia Park
8 minutes' walk
Beautiful park featuring walking trails, duck ponds, and vibrant gardens. A peaceful escape perfect for families.
ScienceWorks Hands-On Museum
ScienceWorks Hands-On Museum
5 minutes' drive
Interactive science museum ideal for families, offering engaging exhibits and hands-on activities. Perfect for curious minds.
Schneider Museum of Art
Schneider Museum of Art
5 minutes' drive
Contemporary art museum featuring rotating exhibitions. Offers free admission on certain days, making art accessible.
Hiking at Grizzly Peak Trail
15 minutes' drive
Scenic hiking trail offering stunning views and nature. Experienced hikers will enjoy the challenge of its terrain.
Yoga at Ashland Yoga Center
10 minutes' walk
Relaxing yoga classes available for all levels. Perfect place to unwind after a day of exploring Ashland.
Alchemy Restaurant and Bar
Alchemy Restaurant and Bar
1 minute' walk
Farm-to-table dining with seasonal ingredients. Renowned for its innovative dishes and eclectic atmosphere.
Paddy Brannans Irish Pub
Paddy Brannans Irish Pub
1 minute' walk
Cozy pub serving hearty Irish fare in a casual setting. Great for families and fans of live music on weekends.
Ashland Playhouse
5 minutes' drive
Local theater featuring films and live performances. Family-friendly shows along with occasional late-night comedy acts.
The Brickroom
5 minutes' walk
Lively bar and music venue offering a variety of events. Great spot for enjoying both local bands and themed nights.
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
Questions of the users
About Winchester Inn
Does the Winchester Inn offer a charging station for Tesla vehicles?
10 November 2024
Yes, there are two charging ports available at the RedTail property located at 500 E Main St.
I'm considering bringing service dogs; are they permitted at the inn?
20 December 2024
Only service animals are accepted at the main property. However, pets can stay at the sister property, 'The Red Tail Inn,' with a pet deposit.
Can I find an ice machine in the hotel, specifically on the main house's top floor?
05 January 2025
The hotel does not have a public ice machine, but guests can request ice from the front desk or restaurant staff, and Housekeeping will refill ice buckets during evening turn-down service.
Are there any accommodations available for those who have difficulty using stairs?
15 February 2025
The inn features six downstairs rooms, including one ADA certified room. Though the others are not certified, many guests with mobility restrictions have enjoyed these rooms.
What is the age requirement for checking into the Winchester Inn?
22 March 2025
Guests need to be at least 21 years old to book a reservation and check in.
Are the amenities at your hotel rated at a certain star level?
30 April 2025
The hotel's amenities generally fall between the 3 and 4 star levels.
What does it mean when a reservation is described as partially refundable?
01 May 2025
The cancellation policy states that prepayments are refunded only if cancellation is made 30 days prior to the scheduled arrival, minus a handling fee. Full payments are required for cancellations made within 30 days or for 'no shows.'
Is there a restaurant available at the Winchester Inn for dining during my stay?
10 June 2025
Yes, the inn boasts two acclaimed restaurants: Alchemy Restaurant and Bar serving craft cocktails and an award-winning wine list, and Chateaubriand 36, a French-inspired steakhouse nearby.
What type of breakfast do guests receive during their stay?
25 July 2025
All guests enjoy a complimentary gourmet breakfast featuring a two-course meal for two.
Are there options for outdoor relaxation at the hotel?
15 August 2025
Yes, guests can enjoy beautiful gardens with various sitting areas perfect for tranquil moments or quiet reading.

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