Stay Realm Logo

Discover

Hotels

Settings

Currency
Language
Loading...
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

E
ElizabethusUS
Verified booking
couple
Standard Room
Stayed in Nov 5, 2025

"Comfortable stay in the heart of Ashland."

10.0

Innkeepers thought of everything to make our stay comfortable. We had a lovely room(Sylvan)with window seat and sitting area. The breakfast was outstanding and the location convenient to theaters and restaurants.

Nothing

Helpful?
M
MaureenusUS
Verified booking
couple
Standard Room
Stayed in Oct 30, 2025

"Beautiful Inn - the food is delicious and the location is great."

8.0

Location and breakfast was great. The room size was quite large.

It was a cold and rainy weekend and I was looking forward to taking a hot bath. The jets on the jacuzi tub were filled with black mold that formed a film on the surface. Not happy. We were comped $75 for the inconvenience.

Helpful?
Y
YIQINGusUS
Verified booking
couple
Standard Room
Stayed in Oct 29, 2025

"Exceptional"

9.0
Helpful?
R
RicciusUS
Verified booking
couple
Standard Room
Stayed in Oct 26, 2025

"We had a very relaxing last two days staying at the inn before heading home to Portland. Thank you."

10.0

My husband and I I were finishing a two week road trip staying our last two nights at the Winchester. We had a lovely room. The breakfast menu was quite extensive. The food was delicious. Our server was attentive. We also had dinner in their restaurant which was a treat.

Helpful?
T
TimothyusUS
Verified booking
couple
Standard Room
Stayed in Oct 26, 2025

"Exceptional"

10.0
Helpful?
B
B9780TBdeborahb
Verified booking
Couples
Standard Room
Stayed in Oct 25, 2025

"Old Inn with modern updates"

10.0

Charming Inn with modern updates. Guest room was large with a comfortable bed. Enjoyed sitting at the table on the small balcony with a nice view of Ashland. Love the extra touches like cookies brought to your room in the late afternoon. We saved them for after dinner at the Alchemy restaurant which is downstairs of the Inn. Delicious dinner with friendly staff. Breakfast was included and it was full service in the dinning room, delicious homemade croissants. We will definitely return!

Helpful?
X
X3381ZWdanc
Verified booking
Family
Standard Room
Stayed in Oct 23, 2025

"Fantastic small hotel!"

10.0

Moved from a very uncomfortable hotel to the Winchester Inn. Both rooms we had were large and comfortable, with terrific bathroom facilities. The included breakfast was outstanding both mornings we were there - serving so much food that we skipped lunch! The staff was friendly and accomodating, and you cannot beat the location. Highly recommended!

Helpful?
L
L4913OVdalek
Verified booking
Couples
Standard Room
Stayed in Oct 17, 2025

"Pretty good, but definitely not worth the price."

6.0

We've stayed here twice. I have to say it's a good place to stay, but not really worth the price, i.e., not a great value. The room was nice, but small, and very clean. It was on the second floor and there is no elevator, so keep that in mind. The front desk staff was exceptionally friendly, but no one was there any of the 3 times we went to the front desk. Someone came after a minute on two occasions, but I didn't wait longer than that the 3rd time so left. It was a major inconvenience to have only one key to the room and to get into the building (you need a key 24x7 to enter the building). The gal at the front desk apologized for that but couldn't help us because they literally only one key to that room. I'll state that again, it was a very significant inconvenience that you might not think about until there's two of you with one key and you literally cannot even get into the building without one of the keys. The breakfast was ok, but we think it's a little silly to make it such a production. It's very formal, with a dressed-up waiter, served in 2 courses. I got the meat scramble, which was supposed to have bacon, sausage, and ham. I'm not being dramatic or trying to be over-critical, but I believe there was maybe one tablespoon of meat. My wife and I made a game of "find the bacon" and I was the only one of us to find one piece and it was literally smaller than one-fourth of the size of a dime. It was a very small portion, so I ate something shortly after breakfast (I am 5'8 and weigh about 150 pounds, so I'm obviously not a big eater). My wife ordered the eggs, potatoes, and toast. That's a boring choice, but made more boring by the fact that the potatoes were nothing more than skillet-fried potatoes with zero seasoning that either of us could taste. The location is very good - hard to beat. Overall, the Winchester is a good place to stay, but expensive for what you get and no matter how big the production is for breakfast, it's nothing special.

Helpful?
D
DaleusUS
Verified booking
couple
Standard Room
Stayed in Oct 17, 2025

"Good place to stay, but not worth the price"

7.0

The breakfast was ok, but we think it's a little silly to make it such a production. It's very formal, with a dressed-up waiter, served in 2 courses. I got the meat scramble, which was supposed to have bacon, sausage, and ham. I'm not being dramatic or trying to be over-critical, but I believe there was maybe one tablespoon of meat. My wife and I made a game of "find the bacon" and I was the only one of us to find one piece and it was literally smaller than one-fourth of the size of a dime. It was a very small portion, so I ate something shortly after breakfast (I am 5'8 and weigh about 150 pounds, so I'm obviously not a big eater). My wife ordered the eggs, potatoes, and toast. That's a boring choice, but made more boring by the fact that the potatoes were nothing more than skillet-fried potatoes with zero seasoning that either of us could taste.

The room was on the second floor and there is no elevator, so keep that in mind. The front desk staff was exceptionally friendly, but no one was there any of the 3 times we went to the front desk. Someone came after a minute on two occasions, but I didn't wait longer than that the 3rd time so left. It was a major inconvenience to have only one key to the room and to get into the building (you need a key 24x7 to enter the building). The gal at the front desk apologized for that but couldn't help us because they literally only one key to that room. I'll state that again, it was a very significant inconvenience that you might not think about until there's two of you with one key and you literally cannot even get into the building without one of the keys.

Helpful?
L
LizusUS
Verified booking
couple
Standard Room
Stayed in Oct 16, 2025

"Beautiful historical property with a wonderful restaurant."

10.0

Beautiful historical property.

Nothing.

Helpful?