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

C
Cathompson5MEDFORD, OREGON
Verified booking
Couples
Standard Room
Stayed in Jan 10, 2026

"Truly enjoyable"

10.0

The bed and the pillows are incredibly comfortable. It’s difficult to get out of bed in the morning, but worth it for the breakfast that is insanely good. Portions for the breakfast are amazing and the taste is really exceptional. We love everything about this place and have stayed a few times now. Everyone is really kind, check-in is really easy, location is perfect.

Helpful?
K
KyrausUS
Verified booking
couple
Standard Room
Stayed in Jan 10, 2026

"A gem in the off season!"

10.0

Outstanding breakfast, lovely grounds, loved the fireplace in our room. Off season it’s a great deal and wonderful place to stay. Wouldn’t be able to experience this place in high season.

Only complaint we had was the plethora of placards in the room. Putting all the instructions, menus etc would have been been much nicer in a nice book. Would be nice if could encourage other guests not to slam their doors. You wouldn’t think you’d need to tell people to be considerate but seems it’s needed.

Helpful?
T
TedusUS
Verified booking
couple
Standard Room
Stayed in Jan 10, 2026

"Exceptional"

9.0

Charming place, wonderful people, really good food.

Helpful?
C
CynthiausUS
Verified booking
solo_traveller
Standard Room
Stayed in Jan 9, 2026

"Walk to everything you want to see in downtown Ashland."

8.0

Great location & very nice staff

Helpful?
D
DebbieusUS
Verified booking
couple
Standard Room
Stayed in Jan 6, 2026

"Wonderful as always!!"

10.0

We love everything about the Inn. It is the perfect romantic getaway!

Helpful?
J
JenniferusUS
Verified booking
extended_group
Standard Room
Stayed in Dec 29, 2025

"Wonderful B&B- central location, great value, marvelous breakfast included,"

10.0

Charming lovely place with delicious generous breakfast included - truly wonderful value and memorable stay! This classic beautiful B&B, located just steps away from Main Street in Ashland, transports you back in time to a peaceful vintage past 💐

Everything was perfectly lovely!

Helpful?
D
DensonusUS
Verified booking
couple
Standard Room
Stayed in Dec 29, 2025

"Exceptional"

10.0

the place is beautiful, clean and comfortable.

nothing.

Helpful?
D
DonaldauAU
Verified booking
couple
Standard Room
Stayed in Dec 18, 2025

"Good stay, notwithstanding the poor experience with the breakfast lass."

8.0

A very nice property, good rooms in a good location.

The lass serving the included breakfast had an abrasive personality. She asked questions in a very clipped and unfriendly fashion. She only part-answered questions, not giving complete information. We skipped the breakfast after being treated poorly. We gave both their restaurants (Alchemy and Chateaubriand) a wide berth at dinner time. We had a fantastic (and very friendly) breakfast experience at Brothers Restaurant.

Helpful?
J
JanetusUS
Verified booking
family_with_children
Standard Room
Stayed in Dec 8, 2025

"Perfect"

10.0

Breakfasts were fantastic!

Helpful?
J
JoanneusUS
Verified booking
couple
Standard Room
Stayed in Dec 7, 2025

"Wonderful stay. When in Ashland, Winchester Inn is where I always stay! Fantastic breakfast too."

9.0

Location, comfort, breakfast.

Had dinner at the Alchemy, and the food and cocktails were subpar and overpriced. Toilet seat in Queen Anne needs replacing.

Helpful?
Previous
Next
56
7
89