Book on our site
for up to 10% off
than to Booking.com!
Check rooms and rates
From296US$ /night
Check-in
10Dec2025Select date
Check-out
11Dec2025Select date
Rooms and Guests2 Guests, 1 Room
Key details

Hotel Details

35 South 2Nd Street, Ashland, Oregon, United States, 97520
-
Close to Lithia Park
Perfect
9.5
9.7
/10
4.8
/5

Pros

Multiple room configurations with private entrances and garden views

On-site coffee bar and outdoor patio dining

Evening turndown service and same-day laundry available

Within walking distance to local theaters and shopping

Cons

18.5 miles distance from nearest airport

11 AM checkout time may be early for some guests

View all

Select room type

Choose from double rooms, family suites, and premium stays. Enjoy breakfast, flexible cancellations, and exclusive deals.
Comfort Triple Room Shower
2 persons
33 m² 
1 King-size bed
Shower
Coffee machine
Double Room Garden View
2 persons
33 m² 
1 King-size bed
Shower
Coffee machine
Standard Queen Room
2 persons
28 m² 
1 King-size bed
Shower
Coffee machine
Queen Room
2 persons
33 m² 
1 King-size bed
Shower
Coffee machine
Click button to see more rooms
Show all rooms
Show all roomsLess

Check Availability & Prices

Find the best rates for your travel dates now!

Facilities

Hotel has comfortable rooms, premium services, and a prime downtown location

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 exceptional dining experiences that celebrate local flavors and culinary artistry. With cozy ambiances perfect for any occasion, guests can enjoy an impressive array of dishes and craft cocktails while soaking in the vibrant atmosphere.
Winchester Inn Ashland Restaurant photo

Alchemy Restaurant and Bar

American, French, and International
Ambiance
Modern and Romantic
Key Offerings
Savor gourmet offerings, including vegetarian, gluten-free, and dairy-free options. Revel in a curated wine selection recognized with a Best of Award of Excellence from the Wine Spectator.
Reservation
Recommended
Tuesday to Saturday, 4:00 PM - 9:00 PM

Chateaubriand 36

French Steakhouse
Ambiance
Family-friendly
Key Offerings
Indulge in expertly prepared steak dishes in a welcoming environment that caters to families. This intimate dining space is perfect for shared meals and 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
390 m
Library
Ashland Library
250 m
Library
Ashland
300 m
111 E Main St
Zagorska Oasis
340 m
Store
Ashland Food Co-op
530 m
Park
Bluebird Park
550 m
264 E Main St
Prize
140 m
Gallery
Ashland Art Center
170 m
N Main St
Lithia Fountains
470 m
Store
Northwest Nature Shop
520 m
N Main St
Downtown Plaza
540 m
Restaurants
Alchemy Restaurant and Bar
10 m
35 S 2nd St at the Winchester Inn
Smithfields Restaurant and Bar
50 m
36 South 2nd Street
Paddy Brannans Irish Pub
50 m
23 S 2nd St
Pangea
110 m
272 E Main St
Hearsay Restaurant
120 m
40 S 1st St
Cafe Aroma & AromaDome Wellness Center
90 m
296 E Main St
Pie + Vine
130 m
358 East Main Street
Redzone Sports Bar N Grill
100 m
303 E Main St
The Village Baker of Ashland
160 m
372 E Main St
Explore Ashland
Local Activities and Dining
Top Attractions
Activities
Dining
Entertainment
Oregon Shakespeare Festival
Oregon Shakespeare Festival
5 minutes' walk
Renowned theater showcasing world-class performances, located just steps from the hotel.
Lithia Park
Lithia Park
8 minutes' walk
Scenic park featuring beautiful gardens, walking trails, and a tranquil pond. Perfect for a leisurely stroll.
ScienceWorks Hands-On Museum
ScienceWorks Hands-On Museum
5 minutes' drive
Interactive science museum great for all ages, offering hands-on exhibits and educational programs.
Schneider Museum of Art
Schneider Museum of Art
5 minutes' drive
Contemporary art museum featuring rotating exhibits and an impressive collection of modern art.
Hiking at Grizzly Peak Trail
10 minutes' drive
Challenging trail with stunning views. Ideal for thrill-seekers who enjoy outdoor adventures.
Yoga at local studios
10 minutes' walk
Relaxing yoga classes available at nearby studios, offering various styles for all experience levels.
Visit North Mountain Park
5 minutes' drive
Nature park with trails, a nature center, and picnic areas. Great for family-friendly outings.
Alchemy Restaurant and Bar
Alchemy Restaurant and Bar
1 minute' walk
Fine dining with a focus on local ingredients. Known for its innovative dishes and inviting atmosphere.
Smithfields Restaurant and Bar
Smithfields Restaurant and Bar
1 minute' walk
Casual dining with a relaxed vibe, serving Southern-inspired dishes and a fine selection of wines.
Paddy Brannans Irish Pub
Paddy Brannans Irish Pub
1 minute' walk
Welcoming pub atmosphere featuring hearty Irish fare and live music, perfect for unwinding after a long day.
Oregon Shakespeare Festival
Oregon Shakespeare Festival
5 minutes' walk
Watch a range of performances from Shakespeare to contemporary plays in an engaging atmosphere.
Local Music Venues
5 minutes' walk
Enjoy live music ranging from jazz nights to local bands at nearby intimate venues.
Ashland Library
Ashland Library
4 minutes' walk
Community library hosting events and activities for all ages, perfect for family-friendly outings.
Getting around
City Centre
Ashland4 min  ·  300 m
Airports
Rogue Valley International-Medford (MFR)39 min  ·  25.7 km
Klamath Falls (LMT)158 min  ·  105.2 km
Bus
Bus stop3 min  ·  200 m
Unlock Exclusive Early Booking Rates
Plan ahead and get special discounts now!
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 are the check-in and check-out times at Winchester Inn?
Check-in is at 16:00 and check-out is by 11:00.
Is parking available at Winchester Inn?
Free private parking is available on-site without reservation.
What is the distance from Winchester Inn to Rogue Valley International-Medford Airport?
The hotel is located 30 km from Rogue Valley International-Medford Airport.
What is included in the breakfast at Winchester Inn?
Guests can enjoy a complimentary two-course gourmet breakfast each morning.
Are there dining options on-site at Winchester Inn?
The hotel features an award-winning restaurant, Alchemy, which serves a full range of meals and drinks.
Which room amenities does Winchester Inn offer?
Rooms are equipped with air conditioning, flat-screen TVs, coffee makers, and free WiFi.
What activities can guests enjoy at Winchester Inn?
Guests can participate in hiking and tennis during their stay.
What popular attractions are near Winchester Inn?
Nearby attractions include the Oregon Shakespeare Festival (0.5 km), Lithia Park (0.5 km), and Southern Oregon University (2 km).
What languages do the staff speak at Winchester Inn?
The staff primarily speak English.
What are the options for nearby dining around Winchester Inn?
Nearby restaurants include Larks Home Kitchen Cuisine, Hearsay Restaurant, and NW Raw, all located within 0.5 km.
Does Winchester Inn have outdoor areas for guests?
Guests can enjoy the gardens and an outdoor patio area at the hotel.
What types of accommodations does Winchester Inn offer?
The hotel offers a variety of accommodations, including suites and cottages with unique features.

Next best alternative

Consider them for your next trip.
Check-in
10Dec2025Select date
Check-out
11Dec2025Select date
Rooms and Guests2 Guests, 1 Room
Need more options?
Check Top hotels near Winchester Inn
The Columbia Hotel Ashland Room photo
Mobile-only price

The Columbia Hotel Ashland

7.2
Very good14 reviews
89m from property
USD 144USD 129
per night
Ashland Springs Hotel Skyline photo
Mobile-only price

Ashland Springs Hotel

8.5
Great407 reviews
138m from property
USD 98USD 88
per night
The Matriarch Suites- Downtown Ashland, Or Exterior photo
Mobile-only price

The Matriarch Suites- Downtown Ashland, Or

9.2
Perfect63 reviews
313m from property
USD 179USD 161
per night