Menu

Winchester Inn

eeef - (888) 608-6346
Winchester Inn, 35 South 2nd Street, Ashland, OR -(888) 608-6346
Area: Ashland
(Map)
4.75
HOTEL RATING: 
EXCEPTIONAL
4.75 out of 5 (589 Ratings)
0.4 miles Ashland Armory
t7 mins walking
BOOK ONLINE OR CALL - (888) 608-6346
Show Prices
Hotel Description
Located in Ashland, a 2-minute walk from Oregon Cabaret Theatre, Winchester Inn has accommodations with a garden, free private parking, a restaurant and a bar. Among the facilities at this property are a concierge service and luggage storage space, along with free WiFi throughout the property. Certain accommodations at the property have a balcony with a mountain view. The rooms come with air conditioning, a flat-screen TV with cable channels, a fridge, a coffee machine, a shower, free toiletries and a closet. Rooms have a private bathroom with a hairdryer, while certain rooms come with a terrace and others also feature city views. The rooms in the hotel are equipped with bathrobes and an iPod docking station. Breakfast is available, and includes à la carte, Full English/Irish and American options. You can play tennis at Winchester Inn, and the area is popular for hiking. Popular points of interest near the accommodation include Ashland Library, Oregon Shakespeare Festival and Lithia Park. Rogue Valley International-Medford Airport is 24 miles from the property.

Check-in time: 16:00   Check-out time: 11:00
Enter Your Dates
4
4
CHECK IN
 
CHECK OUT
 
7
1 room
7
2 guests
Amenities View More
y
Free Internet
j
Free Parking
w
Non Smoking
q
Accessible
x
Free Breakfast
u
Swimming Pool
E
Fitness Center
A
Business Center
B
Airport Shuttle
r
Pets Allowed
Other Amenities
` Free Parking
` Garden
` Golf Course
` Meeting/Banquet Facilities
` Room Service
` Air Conditioning
` Bar
` Hiking
` Heating
` Fax/photocopying
` On-site parking
` Accessible parking
` Concierge services
` Family Rooms
` Free Wi-Fi
` Off-Site parking
` Restaurant(s)
` Daily Housekeeping
` Happy Hour
` Non-Smoking Rooms Available
` Wine/champagne
` Outdoor furniture
` Themed dinner nights
` Key access
` Smoke alarms
` Fire extinguishers
` Guests can opt-out of daily cleaning service
` Staff follow all safety protocols as directed by local authorities
` Shared stationery such as printed menus, magazines, pens, and paper removed
` Cashless payment available
` Linens, towels and laundry washed in accordance with local authority guidelines
` Hand sanitizer in guest accommodation and key areas
` Invoices
` All plates, cutlery, glasses and other tableware have been sanitized
` Free face masks
` Food delivery
` Daily disinfection
` Facilities for disabled guests available
` Laundry services
` Luggage storage & lockers
` Non-smoking property
` Restaurant (special diets available)
` Tennis court & equipment
` Physical/social distancing guidelines
` Protective screen or physical barriers in appropriate areas
` Allergy-free rooms available
` Takeout dining services available

Winchester Inn Guest Reviews

Overall Average Score: 
Exceptional (4.75 out of 5)

Write a review

4.5

Wonderful - 4.5 out of 5

Kathleen Thu, 14 August 2025

Superb

4.5

Wonderful - 4.5 out of 5

Miriam Tue, 12 August 2025

If staying in Ashland, the...

Liked: We love this inn & have stayed there many times. The staff is wonderful & food exceptional.
Disliked: We did not like our room this last time & will choose one we have stayed in before. This room was smaller & difficult to get around.

5

Exceptional - 5.0 out of 5

Wendy Tue, 12 August 2025

Exceptional

5

Exceptional - 5.0 out of 5

Simpson Tue, 12 August 2025

Exceptional

5

Exceptional - 5.0 out of 5

Peter Sun, 10 August 2025

Perfect for theater goers.

Liked: Central location with easy access to OSF theaters. Very comfortable room, lovely breakfast. Would stay here again.

4.5

Wonderful - 4.5 out of 5

Bridget Wed, 6 August 2025

Beautiful and charming Victorian-style inn...

Liked: Beautiful property, charming room, great location, tasty made-to-order (not a buffet!) breakfast. Easy and safe parking.
Disliked: I received a great last minute discount from Booking.com for this room. It would have been out of my price range otherwise.

4

Very Good - 4.0 out of 5

Anna Wed, 6 August 2025

Beautiful dreamy inn with beds...

Liked: The room was beautiful (bright and spacious and great location) and the breakfast is far beyond what any normal breakfast at a hotel is.
Disliked: The bed is simply too soft and not supportive. If people traveling have any back issues and need a supportive bed this may not be the place for you. We stayed here two years ago (when my back wasn’t as bad) and I recall the bed being quite soft. This time I had to make the pull out sofa in the middle of the night to fall asleep

5

Exceptional - 5.0 out of 5

Grafiada Tue, 5 August 2025

Exceptional

Liked: This was the most beautiful hotel! The owners and staff paid attention to elevate every detail.
Disliked: There was nothing to criticize. I will stay longer on my next stay.

4.5

Wonderful - 4.5 out of 5

Kathleen Fri, 1 August 2025

Superb

2.5

Fair - 2.5 out of 5

Anonymous Thu, 31 July 2025

Not what i expected.

Liked: Great location. Friendly staff and good breakfast!
Disliked: It’s very old. Creaky floor, full carpet and small room.

Write a Review of Winchester Inn
Trip Id (Required)
Your Name (Required)
Your City
Your Email Address (Required)
Your overall rating of Winchester Inn
What was good?
What was bad?
Your review of Winchester Inn
Winchester Inn 35 South 2nd Street, Ashland, OR