Book directly with us
up to 10% cheaper
than with Booking.com
Check rooms and rates
From296US$ /night
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

Property overview

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

Rooms and Cottages

The Winchester Inn provides 21 rooms, suites, and cottages. Rooms include queen or king beds, flat-screen TVs, honor bars, Antica Farmacista toiletries, and robes. Guests receive a 2-course gourmet breakfast for two. Suites feature soaking tubs or jacuzzi baths. Select rooms include seating areas. Cottages have private entrances. Each room features fresh flowers and afternoon pastry treats.

On-Site Dining

Alchemy Restaurant and Bar is located on the main floor. The restaurant serves lunch and dinner. Alchemy is critically acclaimed for its kitchen and offers a wine and cocktail program featuring a Best of Award of Excellence from the Wine Spectator. The bar opens at 4:00 PM, and the restaurant opens at 5:00 PM. Chateaubriand 36, a French-inspired steakhouse, is located across the street.

Leisure and Location

The Winchester Inn is located near the Oregon Shakespeare Festival and the Oregon Cabaret Theater. Guests can enjoy gardens with sitting areas. Paschal Winery and StoneRiver Vineyards are also nearby. The Rogue Valley International-Medford Airport is 30 km away. Landmarks nearby include Ashland Food Co-op (0.5 km), Ashland Library (0.3 km), and ScienceWorks Hands-On Museum (2 km).

Hotel Services

The Winchester Inn provides high-speed wireless internet access throughout the property. Guests will be provided a 2-course gourmet breakfast. Rooms are serviced twice daily by housekeeping. Additional services include morning-through-evening valet service and same-day laundry service. The hotel features a coffee bar.

Events and Activities

The Winchester Inn is a backdrop for events, with space for meetings up to 30 people. The Oregon Shakespeare Festival is nearby and presents plays, backstage tours, and educational programs. The Ashland Chamber of Commerce provides information on area events and activities.

“The award-winning dining is reason enough to visit, but it's the uniquely personal service that sets it apart. This historic inn cultivates a romantic atmosphere, further enhanced by gourmet breakfasts and well-appointed rooms. It's a distinctive Ashland experience, ideally situated for those drawn to the Oregon Shakespeare Festival.”
Hotel logo
Victoria GableEditor, UsPacificnorthwest
View all

Choose your preferred room

The property features double rooms, family rooms, and suites, often including breakfast, free cancellation, and special offers
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
Show all rooms
Show all roomsLess

View our availability and price calendar

See current availability and pricing for your dates

Facilities

Amenities for a comfortable stay

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

Dining Onsite

Winchester Inn boasts diverse dining experiences that celebrate local flavors and international cuisines. Guests can relish gourmet meals in a modern setting or enjoy hearty family-style dinners, complemented by an inviting outdoor patio. The carefully curated offerings cater to various dietary preferences, ensuring delightful indulgence for all tastes.
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
A sophisticated menu featuring vegetarian, gluten-free, and dairy-free options, paired with a celebrated wine list recognized by Wine Spectator and a notable cocktail program.
Reservation
not needed
Tuesday to Saturday, 4:00 PM - 9:00 PM; gourmet breakfast included.

Chateaubriand 36

French, Steakhouse
Ambiance
Family friendly
Key Offerings
A cozy dining spot ideal for family dinners, serving expertly prepared steaks alongside classic French dishes.
Reservation
recommended
Wednesday to Saturday, 5:00 PM - 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
Experience Ashland
Top Attractions
Activities
Dining
Entertainment
Oregon Shakespeare Festival
5 minutes' walk
Renowned theater company featuring world-class performances. A cultural highlight in Ashland with various productions year-round.
Lithia Park
8 minutes' walk
A beautiful, expansive park with gardens, playgrounds, and walking trails, perfect for a leisurely day outdoors.
ScienceWorks Hands-On Museum
5 minutes' drive
An interactive science museum with exhibits for families and kids. Great for a fun and educational experience.
Schneider Museum of Art
5 minutes' drive
A contemporary art museum showcasing rotating exhibits and unique installations. Perfect for art enthusiasts.
Grizzly Peak Trail
10 minutes' drive
Challenging hike with breathtaking views of the surrounding mountains. Great for adventure seekers and nature lovers.
Yoga Classes at Ashland Yoga Center
5 minutes' walk
Relaxing yoga sessions available daily. Perfect for winding down or rejuvenating during your stay.
Alchemy Restaurant and Bar
1 minute' walk
Stylish eatery featuring farm-to-table dishes and artisanal cocktails. Reservations recommended for dinner service.
Paddy Brannans Irish Pub
1 minute' walk
Casual pub atmosphere with hearty Irish fare and a diverse drink menu. Enjoy live music on select nights.
The Armory
5 minutes' walk
A vibrant venue hosting live music, comedy shows, and events. Family-friendly options available throughout the year.
Ashland Elks Lodge
10 minutes' walk
Home to community events and dances. Join in for a fun evening of local entertainment and camaraderie.
Local transportation
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
Planning ahead? Check our early rates
Access special offers today
Check Rates
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
FAQs
About Winchester Inn
What is the check-in and check-out policy at Winchester Inn?
Check-in is at 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 type of amenities are available in the rooms at Winchester Inn?
Rooms are equipped with air conditioning, a flat-screen TV, a fridge, a coffee machine, free WiFi, and premium bedding.
What dining options are offered at Winchester Inn?
The hotel features an on-site restaurant, Alchemy, which offers award-winning dining and serves breakfast, lunch, and dinner.
Are there any nearby restaurants to Winchester Inn?
Nearby restaurants include Larks Home Kitchen Cuisine, Hearsay Restaurant, NW Raw, Pangea, and several others, all located within 0.5 km.
Is parking available at Winchester Inn?
Free private parking is available on-site without the need for reservations.
What recreational activities are available at Winchester Inn?
Guests can enjoy tennis and hiking in the surrounding area.
What type of breakfast does Winchester Inn offer?
A complimentary two-course gourmet breakfast is provided for all guests.
Which popular attractions are close to Winchester Inn?
The hotel is within walking distance of the Oregon Shakespeare Festival, Lithia Park, and Ashland Library.
What are the key highlights of Winchester Inn?
Highlights include an award-winning restaurant, historic charm, free Wi-Fi, and a lounge bar.
What kind of views can guests expect from rooms at Winchester Inn?
Certain rooms provide balconies and scenic views of the mountains.
What language is spoken by the staff at Winchester Inn?
The staff primarily speaks English.

Next best alternative

Consider them for your next trip.
Check-in
14Feb2026Select date
Check-out
15Feb2026Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near Winchester Inn
Ashland Springs Hotel Skyline photo
Mobile-only price

Ashland Springs Hotel

8.4
Great411 reviews
138m from property
USD 98USD 88
per night
Hanna'S House By Wanderlodges Ashland Room photo
Mobile-only price

Hanna'S House By Wanderlodges Ashland

9.8
Perfect8 reviews
239m from property
USD 151USD 135
per night
Mahar Homes - Plaza North On First Ashland Interior photo
Mobile-only price

Mahar Homes - Plaza North On First Ashland

9.6
Perfect6 reviews
283m from property
USD 308USD 277
per night