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
S
Susanne • extended_group • us
9
2026-10-24 • via Nuitee
A
Ada • solo_traveller • us
10
Decided to stop putting off seeing places. Booked the hotel, a play and were off for a 3 day road trip. Love Ashland w
Pros:

Beautiful Historical home and the garden was lovely. Close to the theater and downtown. We didn’t eat there but it smelled amazing.

2026-10-23 • via Nuitee
L
Lawrence • solo_traveller • us
10
I came to Ashland to be with friends for their wedding. The hotel was fantastic.
Pros:

Wonderful staff. Great room. Perfect location. A. feal boutique hotel.

Cons:

Not much to say about that

2026-10-23 • via Nuitee
D
Doris • couple • us
9
A comfortable and gracious old place with a great location and breakfast!
Pros:

The breakfast at the Winchester B&B is always excellant! It is a big part of why we stay there. The staff is friendly and helpful and the food is delicious. We've eaten at the on site restaurant before and also enjoyed that. Our room was comfortable and we slept well in our big bed. Watching the sun come up was lovely! The shower was good; lots of hot water and good water pressure.

Cons:

The Winchester B&B is a graceful old place. It has charm but it is worn in places. The carpet on the stairs is dirty, the room smelled musty and the furniture looked worn. We never quite figured out the heater but it wasn't that cold so not a big issue. Despite the quirks we'll probably keep coming back here as we like it overall and it kind of feels like home in Ashland now.

2026-10-22 • via Nuitee
M
Michael • couple • us
9
2026-10-21 • via Nuitee
C
Christey • couple • us
10
2026-10-14 • via Nuitee
M
Markuw1969 • couple • nl
8
Leuke en romantische plek!
Pros:

Leuke plek met leuke uitstraling. Tja, ze hebben het daar goed voor elkaar met restaurant van hoe kwaliteit en aan de overkant ook nog eens een franse bistro volgens mij in eigendom ook. Duidelijk in de hogere prijsklasse en wij konden via Booking een lagere prijs krijgen dan rechtstreeks.

Cons:

Niets

2026-10-08 • via Nuitee
N
Nuray • couple • us
9
Charming hotel in a great location.
Pros:

Lovely property, very close to the OSF, maybe a 7 minute walk. Close to restaurants and other shops downtown. The staff was helpful! The room was huge, with a separate sitting area, the bathroom had a large whirlpool tub and a walk in shower! Breakfast was always delicious and our severs were so friendly!

Cons:

Some stains on the floors and some of the decorative pillows. But honestly not a huge deal. I would recommend bringing some disposable slippers! The stairs were a little daunting as we were in and out of our room several times a days! But overall very minor issues!

2026-10-07 • via Nuitee
P
Paul • couple • us
2
Cons:

I found the staff to be less than forthwright, and even deceiving in the information they provided. If you choose to stay here becareful of what the staff tells you.

2026-09-18 • via Nuitee
C
Corey • solo_traveller • us
9
2026-09-15 • via Nuitee
J
Jill • couple • us
10
2026-09-14 • via Nuitee
G
Giuseppa • solo_traveller • us
10
Pros:

Staff, breakfast

2026-09-14 • via Nuitee
C
Colleen • solo_traveller • us
10
Wil definitely stay again. Service was impeccable.
Pros:

Gorgeous and well maintained

2026-09-10 • via Nuitee
D
Douglas • extended_group • us
10
We had a wonderful weekend stay at Winchester Inn and would definitely return.
Pros:

The room and property were charming and comfortable. We enjoyed the breakfast and had one meal at Alchemy, which was also very good.

Cons:

Everything was great. Parking, I guess, was a little tight, but provided and convenient.
The television in the room was pretty small.

2026-09-08 • via Nuitee
Z
Zoher • extended_group • us
9
2026-09-02 • via Nuitee
S
Sherry • couple • us
8
Short one night stay, it was comfortable & great location
Pros:

Great location. Lovely little place. Our room was nice. Breakfast was included & you could choose from a menu!

2026-08-31 • via Nuitee
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
N
nayef • solo_traveller • 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