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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

8
822greggSAN FRANCISCO, CALIFORNIA
Verified booking
Family
Standard Room
Stayed in Oct 14, 2025

"A new favorite B&B!!"

10.0

I loved this B&B. We arrived late at night, and the staff were very good about supplying us with all the info we needed to get into our room. Everything was very clean; the staff refreshed daily so we always felt comfy when we returned to our room. The overall grounds are very charming. The main dining area has a wonderful breakfast menu (we ate there 3 mornings and enjoyed all of our meals). Our attic room was so comfy; the bed felt great to sleep in. Given we were on the top floor of one of the buildings, we heard no noise or footfall during our stay. All of the staff were friendly, accomodating, and there were a lot of nice little touches to staying here which you can discover for yourself if you go. It was so close to downtown and the theatres, which made it convenient for our 4-day stay in Ashland.

Helpful?
J
JohnusUS
Verified booking
couple
Standard Room
Stayed in Oct 14, 2025

"Wonderful, and we will be returning to the inn."

8.0

Great location close to restaurants and shops as well as Lithia Park. The breakfast was delicious. Wonderful server and staff. Clean room with comfortable bed.

It’s challenging to reach the second floor with the luggage since there’s no elevator.

Helpful?
D
DianeusUS
Verified booking
couple
Standard Room
Stayed in Oct 13, 2025

"We’ve enjoyed visiting Ashland over the years to break up the drive between California and U of Oregon. The property is"

10.0

Location is ideal. Friendly staff. Food is amazing!

Helpful?
K
KristyusUS
Verified booking
couple
Standard Room
Stayed in Oct 7, 2025

"Exceptional"

10.0
Helpful?
K
KristyusUS
Verified booking
couple
Standard Room
Stayed in Oct 6, 2025

"Delightful stay - staff is so great!"

10.0
Helpful?
T
TheresausUS
Verified booking
couple
Standard Room
Stayed in Oct 2, 2025

"Amazing stay in every way!"

10.0

Our stay here was a huge surprise! What started as just a place to stay while traveling to a mini get-a-way! The entire property was very special from the grounds, to the restaurant, to our room. The staff was really welcoming. There was plenty of coffee in the room and some wonderful house baked cookies waiting for us to enjoy! The room was quiet, the bed comfortable and a pleasure in every way. The staff was especially great! We ate a really fine meal in their restaurant Alchemy and enjoyed a wonderful evening made even more special by our server, Christian! The included breakfast the next day was icing on the cake. It was the best breakfast we had enjoyed in a very long time! The scones may have been the best ever! I just cannot say enough wonderful things about our entire stay.

Absolutely nothing!

Helpful?
P
PatriciausUS
Verified booking
couple
Standard Room
Stayed in Sep 29, 2025

"Exceptional"

10.0

Spacious room - lovely environment!

Couldn’t get a second night.

Helpful?
A
AdrienneusUS
Verified booking
couple
Standard Room
Stayed in Sep 28, 2025

"We would stay again."

9.0

Beautiful property with clean rooms. Location is very convenient to the theaters. Staff was stellar.

Helpful?
J
JoanusUS
Verified booking
solo_traveller
Standard Room
Stayed in Sep 17, 2025

"Winchester Inn is so charming."

10.0

The breakfast was fabulous , service with a smile, and a deer grazing outside. Booking.com price was really a discount!

The Inn is on a hill making it hard to walk. The brick walk up to the door is buckling creating a possible tripping hazard.

Helpful?
A
AlisonusUS
Verified booking
couple
Standard Room
Stayed in Sep 16, 2025

"Exceptional"

10.0
Helpful?
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