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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

H
HindsusUS
Verified booking
couple
Standard Room
Stayed in Mar 24, 2026

"Excellent"

8.0
Helpful?
S
StevenusUS
Verified booking
couple
Standard Room
Stayed in Mar 24, 2026

"Exceptional"

10.0
Helpful?
M
MaryusUS
Verified booking
couple
Standard Room
Stayed in Mar 23, 2026

"Well worth the money."

10.0

Location. Parking on site. Fantastic included breakfast.

Nothing not to like.

Helpful?
Y
Y8371PZlindal
Verified booking
Couples
Standard Room
Stayed in Mar 22, 2026

"Where the Ashland experience has a rooted home with a community of support"

10.0

I don't normally post, but we (husband/self) LOVE this place SO much that I broke my mute-social media rule of not putting me out there/posting. Does 3-5 times staying from out of town each year count for being a fan? I think so. We have stayed at a variety of other GREAT Ashland places (there are so many I could recommend if you can't get into Winchester Inn - and there are legions), but I/he landed on "our place." It's a business (doesn't it have to be?) but you'll overwhelming feel like it's also a community or family home that fits so naturally with the Oregon Shakespeare Festival and local values. This weekend we watched Newbies asking for recommendations and support. Inn staff were extremely well equipped, but everyone also staying there is ready to add recommendations. It's a shared experience at the Winchester Inn. Your planed experience is, and will be, so much richer from engaging with this community and enjoying a stay with them.

Helpful?
K
KathrynusUS
Verified booking
couple
Standard Room
Stayed in Mar 16, 2026

"Exceptional"

10.0

Good central location. Great breakfast

Helpful?
D
DianeusUS
Verified booking
couple
Standard Room
Stayed in Mar 13, 2026

"Off season rates for a fabulous inn."

10.0

Grand home with lovely room and bath. Delicious 2 course breakfast.

All perfect

Helpful?
B
BonitausUS
Verified booking
couple
Standard Room
Stayed in Mar 13, 2026

"Exceptional"

10.0

Lovely Inn with truly amazing staff and services! Alchemy restaurant is located on the property and quite good.

Helpful?
J
JudyusUS
Verified booking
couple
Standard Room
Stayed in Mar 12, 2026

"We loved the location that allowed us to walk around down town. It was very quiet yet close to restaurants , the park an"

10.0

A charming and inviting home. Attention to details that enhanced our stay. Exceptionally clean with a friendly and accommodating staff.

Absolutely nothing.

Helpful?
H
HeidiusUS
Verified booking
solo_traveller
Standard Room
Stayed in Mar 10, 2026

"Exceptional"

10.0

So beautiful like stepping back in time. The grounds are gorgeous, the restaurant is exceptional. The rooms are lovely and beds are very comfortable.

Helpful?
L
LeslieusUS
Verified booking
couple
Standard Room
Stayed in Mar 10, 2026

"Exceptional"

10.0

Beautiful Inn. Everything was picture perfect. Staff was exceptionally. The room was beautiful. The bed was ultra comfy. We will definitely be back!

Helpful?