Free
Children allowed

Facilities

WiFi available
Free WiFi
Parking
Free Parking
Non-smoking rooms
Air conditioning
Restaurant
Heating
Family rooms
Garden
See all facilities

Review Highlights

Pros:
Charming location
Amazing breakfast
Cons:
Old building issues
Staff availability after hours

Categories

Cleanliness
8.49
Some reviews indicated cold breakfasts and issues with old carpeting.
Service
9.96
Generally high praise for helpful and friendly staff, although some service issues mentioned.
Location
10
Repeatedly described as excellent with a charming downtown position.
Room Quality
9.45
Rooms are spacious and comfortable, though some noted age and creakiness.
Amenities
9.48
Amenities like breakfast and bar are highlighted positively, but there were some complaints about the breakfast temperature.
Value for Money
9.44
Value considered high due to included breakfast and overall experience.
Food and Beverage
9.99
Breakfast is frequently praised as outstanding, with mentions of delicious food.
Overall Experience
10
Overall positive sentiment; many patrons express intent to return and high satisfaction.
* This sentiment is summarized by AI based on user reviews.
Updated at: 2026-01-28 06:54

Property Description

Luxurious Accommodations
Winchester Inn, located just 300 metres from the Oregon Shakespeare Festival, offers elegantly appointed rooms with 600 thread count sheets, down feather bedding, and private balconies or patios. The rooms are equipped with modern amenities including flat-screen TVs and air conditioning, ensuring a comfortable stay for all guests.

Gourmet Dining Experience
Guests at Winchester Inn can indulge in a 2-course gourmet breakfast included in their stay, prepared with fresh ingredients. The on-site bar and restaurant with an outdoor patio offer a perfect setting to unwind and enjoy delicious meals. Additionally, a coffee bar is available for guests to grab a quick pick-me-up throughout the day.

Concierge Service and Convenience
The hotel provides concierge service to assist guests with any inquiries or bookings, ensuring a seamless and enjoyable stay. With free parking on-site and proximity to Southern Oregon University and Rogue Valley Airport, Winchester Inn offers convenience and accessibility for all travelers.

Book your stay at Winchester Inn now for a luxurious and memorable experience!

Important information:

Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
Please inform of your expected arrival time in advance. You can use the Special Requests box when booking, or contact the property directly using the contact details in your confirmation.
Managed by a private host
A deposit may be required at the property.

Check-in and check-out hours:
Check-out: 11:00 AM
Airport code: MFR

Location

Guest Reviews

9.6
Based on 659 reviews
Cleanliness: 8.49
Service: 9.96
Location: 10
Room Quality: 9.45
Amenities: 9.48
Value for Money: 9.44
Food and Beverage: 9.99
Overall Experience: 10
J
Janna solo_traveller us
2
2026-08-29 via Nuitee
M
Michael couple us
10
What a delight!
Pros:

Everything about the property--and I mean everything!--was top notch and exceptional: the welcome, the room, breakfast, housekeeping, historic architecture, landscaping, location. We love the place and will make it part of our twice annual trip through Ashland.

Cons:

N/a

2026-08-28 via Nuitee
T
terhi couple us
10
2026-08-27 via Nuitee
K
Kathy couple us
10
Wonderful stay in Ashland.
Pros:

The room had nice morning light, large windows, a comfortable king bed and a large bathroom. We loved having the balcony. Breakfast was excellent.

Cons:

The room was on the second floor and if you aren't good with stairs, this may not be a good choice.

2026-08-27 via Nuitee
N
nayef solo_traveller us
10
2026-08-27 via Nuitee
R
roy solo_traveller us
8
2026-08-22 via Nuitee
H
Harry couple us
10
Great place to stay if you are attending the Oregon Shakespeare Festival.
Pros:

Small, quiet and very convenient to the theaters. Helpful and considerate staff. Excellent restaurants.

Cons:

Very high bed that could be a challenge to get in and out of.

2026-08-16 via Nuitee
J
Joel couple us
10
A Two-night Stay in a 5-star Hotel
Pros:

From the staff to the facility, this rates as a 5 Star hotel. I plan to make this my go-to hotel for future visits.

Cons:

While I gave this the highest possible rating, the bed and sofa bed were very uncomfortable. The main bed was “lumpy” and the sofa bed mattress so thin the metal pieces could be felt.

2026-08-15 via Nuitee
H
Harrison couple us
9
2026-08-14 via Nuitee
K
Karen solo_traveller us
8
2026-08-14 via Nuitee
D
David couple us
9
2026-08-13 via Nuitee
D
Debra couple us
9
2026-08-13 via Nuitee
D
Denise couple us
10
Spectacular accommodations, service and food. Highly recommend.
Pros:

The dinner and breakfast were outstanding. All of the staff were amazing, kind and professional.

Cons:

Nothing!

2026-08-11 via Nuitee
B
Bean solo_traveller us
9
2026-08-09 via Nuitee
R
Ross family_with_children us
9
Great location, nice facility and excellent staff.
Pros:

The breakfast and service were good, but a little more variety day to day would be appreciated.
The room size and location were very good for our needs.

Cons:

The room, the family suite off the driveway was well appointed, but perhaps a little warn. Curb appeal of that suite could be better, but hard to do on the driveway.

2026-08-08 via Nuitee
H
Harrison couple us
10
2026-08-06 via Nuitee
D
Daniel couple sg
8
good place to stay to see the shows
Pros:

high quality furnishing

Cons:

lack of a writing desk

2026-08-04 via Nuitee
J
Jennifer couple us
10
2026-08-04 via Nuitee
L
Leslie couple us
10
2026-08-03 via Nuitee
E
Edward couple it
9
Lovely victorian-style inn close to the Ashland theatres.
Pros:

This is a top-notch property in Ashland, we've visited multiple times before. It's close to the theatres. The breakfasts are very good. The furnishings are largely in an antique style.

Cons:

The breakfast, while free, is full of premium offerings that are not. You are presented every day with a strangely computed bill (with a credit for a free breakfast) to which you are asked to add a tip. I would prefer being asked to add a cumulative tip at check-out. Rooms haven't been updated in a while.

2026-07-24 via Nuitee