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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

C
Chris G. CaliforniausUS
Verified booking
couple
Standard Room
Stayed in Dec 4, 2025

"be aware, they scam you with extra charge."

1.0

The stay at the Hotel was good at the time of stay for 1 night on 10/15/25. But after one month of my stay, my credit card was charged 30.00 for missing a set of keys. This is absolutely false. I didn't got 2 set of keys, I only got 2 keys when I check in. The 2 keys are 1 to the room, and 1 to the building. Hotel charged me 30.00 for extra set of key 1 month later, when I called, they said I only returned 1 set. They didn't bring this up when we return our keys while check-out the room. Now I can only put a dispute with my credit card company. Be aware, this is scam to customer.

Helpful?
E
ErikusUS
Verified booking
couple
Standard Room
Stayed in Dec 3, 2025

"Welcoming and easy at a charming spot in Ashland."

9.0

The Winchester Inn is our new go-to favorite in Ashland and we will book it each time we come through (at least twice a year). The grounds and structure are so very pretty and unique to Ashland. The restaurant, Alchemy, is creative and delicious with the best service. We always feel like we're visiting friends or family when we come to The Winchester and that makes it feel welcoming and easy.

Helpful?
E
ErikusUS
Verified booking
couple
Standard Room
Stayed in Nov 26, 2025

"Comfy, Cozy, Homey with smiles to boot!"

9.0

Winchester Inn has become a favorite spot for us on our way to-and-from the Bay Area (we live in Seattle). The accommodations are comfortable and homey. The service great. The restaurant is excellent for breakfast and dinner!

Helpful?
A
AlexandrausUS
Verified booking
solo_traveller
Standard Room
Stayed in Nov 22, 2025

"Beautiful and charming victorian inn in downtown Ashland."

9.0

Beautiful, cozy inn centrally located. Comfortable, well equipped and quiet room. Wonderful restaurant, Alchemy, on the premises.

Parking could be a little challenging. The property is on a hill. Pillows on my bed were flat.

Helpful?
L
LisausUS
Verified booking
couple
Standard Room
Stayed in Nov 15, 2025

"Well appointed, charming hotel"

10.0

We loved everything about this charming place. The quaint, beautiful hotel, the spacious and comfy room, all the added little touches that make you feel special and well cared for. The breakfast was included, and was not a buffet. The location is one block off the main street, so it is quiet yet well places. The grounds are charming too.

Having to leave!

Helpful?
A
AshinusUS
Verified booking
couple
Standard Room
Stayed in Nov 14, 2025

"Exceptional"

10.0
Helpful?
T
TrinetteusUS
Verified booking
family_with_children
Standard Room
Stayed in Nov 13, 2025

"Exceptional"

10.0
Helpful?
J
JimusUS
Verified booking
extended_group
Standard Room
Stayed in Nov 12, 2025

"Exceptional"

10.0

Excellent location. Everything we wanted to see was within walking distance. Great breakfast.

Helpful?
D
DustinusUS
Verified booking
couple
Standard Room
Stayed in Nov 11, 2025

"Stayed there on a whim. We would definitely stay again"

10.0

The location was great. The inn was cute. The breakfast was amazing with a very friendly staff.

Helpful?
P
PatriciausUS
Verified booking
couple
Standard Room
Stayed in Nov 9, 2025

"Exceptional"

10.0
Helpful?