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
Book on our site
up to 10% cheaper
than Booking.com
Check rooms and rates
From220US$ /night
Check-in
03May2026Select date
Check-out
04May2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

35 South 2Nd Street, Ashland, Oregon, United States, 97520
-
Close to downtown Plaza
Perfect
9.4
9.7
/10
4.9
4.6
/5

The 5-star Winchester Inn Ashland is situated in the historical district of Ashland, around a 25-minute walk from the innovative ScienceWorks Hands-On Museum and features 21 rooms with views of the mountain. A lounge bar as well as a shared lounge and a golf course can be enjoyed at the hotel, boasting the setting not far from the 100-acre Lithia Park.

Location

While staying in this smoke-free hotel, you are invited to discover the Garfield Park, located a mere 1.5 km away, or visit sports venues like Oak Knoll Golf Course, which is 4.8 km away. The Winchester Inn is 300 metres from the Ashland and within a 10-minute drive of the Oredson Todd Woods.

Also, Bluebird Park is situated approximately 600 metres away. Along with other cultural attractions the Ashland Library is nestled a few steps from this accommodation.

The Winchester Inn Ashland is located 30 km from Rogue Valley International-Medford airport and 0.7 km from E Main St - North of 1st St bus stop.

Rooms

All of the allergy-free rooms are complete with an iPod dock and a flat-screen TV with satellite channels, as well as a mini fridge bar, tea and coffee making facilities, and some of them include an adjoining terrace and a balcony. The private bathrooms come with a walk-in shower and a separate toilet.

Eat & Drink

Winchester Inn offers a menu of contemporary cuisine, which you can taste in the American Alchemy Restaurant and Bar restaurant. This Ashland hotel features a restaurant nearby, where guests can enjoy a variety of American cuisine.

Leisure & Business

Active guests will be interested in walking tours arranged by the property.

Must-do experiences

  • Take a stroll through Lithia Park for beautiful scenery and serenity.
  • Visit the Oregon Shakespeare Festival for an unforgettable performance.
  • Savor a gourmet treat at the Ashland Artisan Market every Saturday.
  • Explore the storefronts on Main Street for unique local art and crafts.
  • Try the famous Colombian coffee at Ashland Coffee & Tea for a boost.
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
Garden view
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

Price and Room Availability Calendar

Check availability and prices for your dates now!

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

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
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
Interested in Nearby Hotel Rates?
Live prices. No outdated rates
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
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 243 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 431 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.
Open reviews
Check-in
03May2026Select date
Check-out
04May2026Select date
Rooms and Guests2 Guests, 1 Room