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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

Offsite parking discounted rates available
Parking
Non-smoking rooms
Air conditioning
Restaurant
Family rooms
Luggage storage
Fax/photocopying
Facilities for disabled guests
Non-smoking throughout

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
Exceptional606 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

K
KathleenusUS
Verified booking
couple
Standard Room
Stayed in Jun 18, 2026

"Exceptional"

9.0
Helpful?
H
haiyingusUS
Verified booking
family_with_children
Standard Room
Stayed in Jun 16, 2026

"Very Good"

7.0
Helpful?
J
JohnusUS
Verified booking
couple
Standard Room
Stayed in Jun 12, 2026

"Excellent"

8.0
Helpful?
P
peter grimmusUS
Verified booking
solo_traveller
Standard Room
Stayed in Jun 10, 2026

"Exceptional"

10.0
Helpful?
T
TamarausUS
Verified booking
couple
Standard Room
Stayed in Jun 7, 2026

"Exceptional"

10.0
Helpful?
K
KathleenusUS
Verified booking
couple
Standard Room
Stayed in Jun 5, 2026

"Exceptional"

10.0

Great

Helpful?
W
williambI8017ET
Verified booking
Family
Standard Room
Stayed in May 30, 2026

"Consistently excellent"

10.0

My parents went to Ashland for the plays and stayed at the Winchester for many years, so it was a pleasure to take my dad (now in his mid-90s) for a week to do the same. I can't say enough good things about the Winchester and the restaurant they operate in the evening. High quality service and high quality accommodations, as usual!

Helpful?
K
KarinbeBE
Verified booking
couple
Standard Room
Stayed in May 28, 2026

"Lovely stay in downturn Ashland"

10.0

Wonderful stay - the best bed I ever slept in, in a beautiful room an house, downtown

Breakfast was too much, and the oatmeal was very dry

Helpful?
C
CarolineusUS
Verified booking
couple
Standard Room
Stayed in May 28, 2026

"Fabulous hotel!"

10.0

Beautiful property and gardens. Friendly staff. Delightful breakfast and atmosphere. Super comfortable and quiet rooms. Close walk to Shakespeare festival and fun restaurants and lounges.

N/A

Helpful?
Y
YanousUS
Verified booking
solo_traveller
Standard Room
Stayed in May 28, 2026

"Exceptional"

10.0

Exceeded expectations across the board.

Limited parking

Helpful?
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