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9.6 / 10 Guest Rating

Winchester Inn

35 South 2nd Street, Ashland, us

Winchester Inn - main view

About the Property

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!

Facilities & Amenities

Offsite parking discounted rates available
Parking
Non-smoking rooms
Air conditioning
Restaurant
Family rooms
Luggage storage
Fax/photocopying
Facilities for disabled guests
Non-smoking throughout

Important Information

Check-in & Out

Check-in
Check-out11:00 AM

Property Notes

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. A deposit may be required at the property.

Check Room Availability

1 night · 2 adults

No rooms available

We couldn't find any available rooms for these dates and guests. Try adjusting your search criteria.

Guest Reviews

9.6
Exceptional606 verified reviews
AI Summary

Guests highly rate the charming location and frequently praise the amazing breakfast.

Categories

Cleanliness8.5
Service10.0
Location10.0
Room Quality9.4
Amenities9.5
Value for Money9.4
Food and Beverage10.0
Overall Experience10.0

Select topics to read reviews

I
IaroslavusUS
Verified booking
solo_traveller
Standard Room
Stayed in May 26, 2026

"Exceptional"

10.0
Helpful?
P
PhilipusUS
Verified booking
couple
Standard Room
Stayed in May 26, 2026

"Good stay in a well-maintained Victorian mansion"

10.0

We had a nice lower floor room which was pleasantly decorated. Staff was friendly and helpful. Location is good... Quiet but close enough to OSF and downtown to walk everywhere. Hearty breakfast included.

Although comfortable enough, the bed mattress had a soft surface. I prefer a firmer one but it did not detract from our visit.

Helpful?
M
martysI7076XB
Verified booking
Couples
Standard Room
Stayed in May 14, 2026

"Our "go to" place to stay in Ashland"

10.0

The Winchester Inn was a great find for my wife and I. The rooms were spacious, clean, well maintained, comfortable and beautiful. The grounds and gardens are magnificent. And very quite. It was a pleasure to stay here, and this will be or "go to" place anytime we are in Ashland. The restaurant is great, too!

Helpful?
J
JaneusUS
Verified booking
extended_group
Standard Room
Stayed in May 13, 2026

"Perfect location, relaxing atmosphere, excellent accommodation"

9.0

Breakfast was wonderful and the location of the inn was perfect for the Shakespeare Festival and looking around Ashland. Staff were very helpful and the bar was particularly good. Would stay here again without hesitation and would recommend to our friends.

Unfortunately construction was going on close to our room which produced a lot of noise. This was completely outside the control of the inn, so we discounted this inconvenience. Would stay here again

Helpful?
S
ShawnausUS
Verified booking
couple
Standard Room
Stayed in May 4, 2026

"Exceptional"

10.0
Helpful?
A
AnneusUS
Verified booking
couple
Standard Room
Stayed in Apr 28, 2026

"Wonderfully relaxing and beautiful place to stay in Ashland"

10.0

Beautiful inn, rooms with wonderful, thoughtful amenities and lovely garden. Great location if you are coming for the Oregon Shakespeare Festival--can leave your car and just walk to the theater. very close proximity to downtown/shopping district yet feels far away (car and foot traffic). The complimentary breakfast was excellent and nice to have a happy hour even on weekends (with superb bar menu food and reasonably priced drinks). We would definitely plan to stay here again when we come back for the Oregon Shakespeare Festival.

Not much--everything was great. The only minor complaint is our room was directly below the parlor so could hear people walking due to boards squeaking but this was only an issue before dinnertime and not an issue to interfere with sleep or morning hours.

Helpful?
R
RolfusUS
Verified booking
couple
Standard Room
Stayed in Apr 16, 2026

"Exceptional"

10.0
Helpful?
N
NancycaCA
Verified booking
couple
Standard Room
Stayed in Apr 15, 2026

"Very Good"

7.0
Helpful?
G
Verified GuestusUS
Verified booking
couple
Standard Room
Stayed in Apr 13, 2026

"Exceptional"

10.0
Helpful?
D
DavidusUS
Verified booking
couple
Standard Room
Stayed in Apr 12, 2026

"Excellent"

8.0
Helpful?