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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

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

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
Exceptional619 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

M
MartinauAU
Verified booking
couple
Standard Room
Stayed in Jan 24, 2026

"Thoroughly recommend this property for an overnight stop."

8.0

Charming location with well appointed rooms. Huge breakfast.

Pillows were a bit soft for our liking.

Helpful?
N
NancyusUS
Verified booking
couple
Standard Room
Stayed in Jan 22, 2026

"Memorable inn with amazing breakfast. Great location to walk downtown. But you’re kind of on your own after 5 pm in wint"

8.0

Great historic inn with period furnishings. Great location to walk downtown. Breakfast is amazing!!!!!

Carpet needs replacing. No staff around after 5:00 p.m., at least in winter.

Helpful?
E
EleanorusUS
Verified booking
couple
Standard Room
Stayed in Jan 20, 2026

"Lovely room, with fabulous, attached restaurant and bar. Top location. Very classy. Treat yourself!"

10.0

The room was spacious. We had a room with a king bed and an extra single bed, and a large sitting area. Bathroom was spacious and clean with robes for lounging. The breakfast that was included was fabulous. We have stayed here many times. The bar was great and we also had dinner here one night which was a highlight for us. The staff is also extremely friendly and helpful.

We don't have any complaints.

Helpful?
A
AlexausUS
Verified booking
couple
Standard Room
Stayed in Jan 20, 2026

"Winchester is well appointed, great downtown location, and generous amenities"

9.0

The breakfast was disappointing. My meal arrived cold.

Helpful?
A
annausUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Not what i expected."

5.0

Great location. Friendly staff and good breakfast!

It’s very old. Creaky floor, full carpet and small room.

Helpful?
W
WendyusUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Since my husband could have wound up eating walnuts was unacceptable. And there was no effort to."

6.0

My husband had a recorded walnut allergy, and the staff delivered cookies with walnuts. Luckily, I noticed before he ate one. This could have been horrible. They did not offer us anything to replace it. Very disappointing and could have had serious consequences! Also, the bathroom door did not shut.

I got these backwards. See above for dislike. What we enjoyed was the location. The breakfast was deliciius

Helpful?
C
ClaireusUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Exceptional"

10.0
Helpful?
A
amadausUS
Verified booking
couple
Standard Room
Stayed in Jan 19, 2026

"Delightful"

10.0

The location was good and the property itself was beautiful. Our bed was very comfortable and our room was oversized and very clean. The breakfast was amazing.

Helpful?
K
KristymxMX
Verified booking
extended_group
Standard Room
Stayed in Jan 17, 2026

"I would stay at the Winchester each time I was in Ashland, if I could. No better place around!"

10.0

I've stayed at the Winchester many times in the past. This trip was much like the others. The room was sparkling clean. The Breakfast was the best breakfast you could get, which is included in the room price. A fabulous choice on the menu. In the room there are great little things waiting for you like, home made cookies, which are amazing; a variety of teas; coffee and a bottle of wine (which you pay for). We couldn't ask for anything more on top of the beautiful grounds and the antique environment, you might expect a horse & carriage to come pick you up.

I liked everything, I must admit!

Helpful?
M
MatthewusUS
Verified booking
couple
Standard Room
Stayed in Jan 13, 2026

"This is our third time here. We will be back"

10.0

Location is excellent, right in the middle of town. Able to walk to most things. The breakfast is outstanding.

We liked everything

Helpful?
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