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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

N
NikalausUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 9, 2026

"Exceptional"

10.0
Helpful?
A
AnausUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 8, 2026

"Couples Bucket List !!!!"

10.0

Breakfast is the best I have ever had ! Every meal was prepared perfectly

There is nothing to add

Helpful?
A
amandausUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 6, 2026

"Cozy, incredible, delicious. One of (if not the) best places I've ever stayed."

10.0

The complimentary breakfast is insane! SO delicious and high-end, I plan to stay here at least five more times just to try everything haha But really, this place is nothing short of amazing. The staff, the fresh baked cookies and ice in the room waiting for me, the spa tub, the windows overlooking the city, the boujee feel of the decor, the awesome old staircase leading to my room, absolutely everything about this place is incredible. I am planning another trip to Ashland just to stay here again, it was that awesome. I hope this place and other unique places like it stay in business a very long time.

I have zero complaints, I will say the main door key didn't work that well and I kept having to try and retry opening it, but the staff knows this and I'm sure they will fix it, they obviously pay attention to the needs of the building.

Helpful?
S
S5439WNbg
Verified booking
Solo travel
Standard Room
Stayed in Mar 4, 2026

"Charming in Every Way!"

10.0

I recently enjoyed a two night stay in the Belvedere Suite and it was delightful! The house and grounds are charming, immaculate and obviously well cared for. The inn keepers and team at the Winchester provided impeccable service and with such warmth and genuine kindness. My stay inspired me to slow down, enjoy small moments and read the cozy mystery novel set in the Winchester at their famous Christmas "Dickens Feast". I can't wait to back during the Oregon Shakespeare Festival!

Helpful?
S
SusanusUS
Verified booking
couple
Standard Room
Stayed in Mar 2, 2026

"Excellent breakfast and super nice staff!"

10.0

Wonderful property! Everything top notch. Last minute pricing was a blessing.

Comfy, well supplied, quaint !

Helpful?
B
BonitausUS
Verified booking
couple
Standard Room
Stayed in Feb 24, 2026

"A not to miss lodging experience in Ashland."

10.0

Lovely property and gracious staff. Extra touches such as cookies in the room, ice in ice bucket, phone call to relay room was ready for early check in. Complimentary breakfast was fabulous!

Helpful?
S
SueusUS
Verified booking
couple
Standard Room
Stayed in Feb 22, 2026

"Exceptional"

10.0

The free breakfast was a culinary delight! Off season prices were extremely reasonable.

Helpful?
K
KevinusUS
Verified booking
solo_traveller
Standard Room
Stayed in Jan 30, 2026

"Exceptional"

10.0

Extra touches, cookies at 3:00PM. Good washing accessories

Helpful?
J
JanetusUS
Verified booking
couple
Standard Room
Stayed in Jan 27, 2026

"Exceptional"

10.0

Everything!

Helpful?
E
EarthausUS
Verified booking
couple
Standard Room
Stayed in Jan 25, 2026

"Excellent"

8.0
Helpful?