Air Conditioner
Parking
View
Wheelchair Accessible
Balcony/Terrace
Accessibility
Security/Safety
Business Services
Sports/Activities
Restaurant
Bar
Guest Services
Entertainment
Breakfast
Child Friendly
Heating
Internet
Laundry
Historic Charm
Winchester Inn in Ashland offers a historic setting with a beautiful garden, tennis court, and free WiFi. The property features a family-friendly restaurant, bar, and outdoor seating area.
Comfortable Accommodations
Rooms include air-conditioning, private bathrooms, and modern amenities such as mini-bars and flat-screen TVs. Additional facilities include a terrace, balcony, and spa bath.
Dining Experience
Guests enjoy a variety of breakfast options including American, full English/Irish, and continental. The restaurant serves French, American, and local cuisines in a modern and romantic ambiance.
Prime Location
Located 24 mi from Rogue Valley International-Medford Airport, the inn is near Oregon Cabaret Theater (2-minute walk), Oregon Shakespeare Festival (4-minute walk), and Lithia Park (1969 feet). An ice-skating rink is also nearby.
Winchester Inn is located in Ashland.
This 25 Bedrooms Hotel is suitable for
tourists and travelers.
It has several amenities that would guarantee your comfort. These amenities include:
Air Conditioner, Parking, View, and several others.
This is a 5 star rated property and has over 409 reviews
with the average score of 9.4
.
Coming to Ashland and needing a place to stay?
Be it for work or for leisure, consider staying at this Hotel for your next visit,
you will surely love it.
You can check the reviews and description of this 25 Bedrooms Hotel
if you want to learn more about this Sonder place in Ashland. These details are
authentic, as they are provided by our partner, booking.com.
This Winchester Inn in Ashland is well equipped and has all
facilities that have been listed below.
Please note that these details were shared to us by booking.com for the listed
“Winchester Inn”.
We solely rely on their shared details and are regarded as “accurate”. If you have any concerns about the
information or accuracy describing this
Hotel, please let us know.
Arrivals & Check-in
Contactless check-in, practical layout, settle straight in
Hotel · Ashland
Arrival
The minimum age for check-in is 18
Design
461.91 ft²,
25 Bedrooms
Bath products
24 Bathrooms
Tech
WiFi and entertainment where listed in amenities
Bedrooms & Baths
Compact stay with a practical layout
Where you sleep
· 25 Bedrooms
· 24 Bathrooms
Wine/Champagne
Bar
Restaurant
Special diet meals (on request)
Street parking
Parking on site
Parking
Free parking
Private Parking
Accessible parking
Property Amenities
Comforts and facilities at this stay
Air Conditioner
Internet
Child Friendly
Parking
Accessibility
Business Services
Guest Reviews
Winchester Inn Reviews
“Great place to stay if you are attending the Oregon Shakespeare Festival.”
Read More
Harry
·
Aug 16, 2026 07:00:00 AM
“A Two-night Stay in a 5-star Hotel”
Read More
Joel
·
Aug 15, 2026 07:00:00 AM
“Lovely stay in downturn Ashland”
Read More
Karin
·
May 28, 2026 07:00:00 AM
View more reviews
Winchester Inn Reviews
“Great place to stay if you are attending the Oregon Shakespeare Festival.”
Harry
·
Aug 16, 2026 07:00:00 AM
“A Two-night Stay in a 5-star Hotel”
Joel
·
Aug 15, 2026 07:00:00 AM
“Lovely stay in downturn Ashland”
Karin
·
May 28, 2026 07:00:00 AM
“Fabulous hotel!”
Caroline
·
May 28, 2026 07:00:00 AM
“Exceeded expectations across the board.”
Yano
·
May 28, 2026 07:00:00 AM
“Good stay in a well-maintained Victorian mansion”
Philip
·
May 26, 2026 07:00:00 AM
Good to know · before you book.
Check-in
The minimum age for check-in is 18
Cancellation Policy
Non refundable
Pet Policy
Pets are not allowed
Stay length
1 Night minimum.
Other Policy
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.
Booking
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FAQs
Frequently asked questions
01 / 08
Is this Winchester Inn pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
02 / 08
What time is check-in & check-out at Winchester Inn?
Check-in time for Winchester Inn starts counting from 4:00 PM and check-out is until 11:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
03 / 08
Does the Winchester Inn have a swimming pool?
No, this Winchester Inn does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
04 / 08
How much does it cost per night to stay in Winchester Inn?
Best-rates for the Winchester Inn starts from $184 per night with includes Air Conditioner, Parking, View, Wheelchair Accessible, Balcony/Terrace, Accessibility, Security/Safety, Business Services, Sports/Activities, Restaurant, Bar, Guest Services, Entertainment, Breakfast, Child Friendly, Heating, Internet, Laundry with all other facilities. Sonder is dedicated to ensuring every traveler enjoys a comfortable and exceptional stay, whether traveling solo, with a partner, with a pet, or with the whole family.
05 / 08
Is Winchester Inn a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 5 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
06 / 08
Is the Winchester Inn wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Winchester Inn is wheelchair accessible. Likewise, there is an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
07 / 08
What is the minimum night stay policy for the Winchester Inn?
Based on the information reported by the owner or manager, the Winchester Inn indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
08 / 08
What cancellation policy is in place for Winchester Inn?
Based on the information reported by the owner or manager, details for the cancellation policy for the Winchester Inn are as follows: Non refundable Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Check-in time for Winchester Inn starts counting from 4:00 PM and check-out is until 11:00 AM. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
No, this Winchester Inn does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
Best-rates for the Winchester Inn starts from $184 per night with includes Air Conditioner, Parking, View, Wheelchair Accessible, Balcony/Terrace, Accessibility, Security/Safety, Business Services, Sports/Activities, Restaurant, Bar, Guest Services, Entertainment, Breakfast, Child Friendly, Heating, Internet, Laundry with all other facilities. Sonder is dedicated to ensuring every traveler enjoys a comfortable and exceptional stay, whether traveling solo, with a partner, with a pet, or with the whole family.
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this hotel 5 stars or guests have recommended them suitable for families. As reported by the owner or manager, the hotel has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Based on the information received from our partner, the Winchester Inn is wheelchair accessible. Likewise, there is an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
Based on the information reported by the owner or manager, the Winchester Inn indicates 1 day stay policy at this hotel. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
Based on the information reported by the owner or manager, details for the cancellation policy for the Winchester Inn are as follows: Non refundable Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
Neighborhoods of Historic Downtown District
Every few blocks, a different Historic Downtown District.
From historic streets to leafy waterfront, each neighborhood offers its own way to spend a day in the city.
35 South 2nd Street, Ashland, OR 97520, USA
409 reviews
Hotel Suite
Air Conditioner
Parking
View
Wheelchair Accessible
Balcony/Terrace
Accessibility
Security/Safety
Business Services
Sports/Activities
Restaurant
Bar
Guest Services
Entertainment
Breakfast
Child Friendly
Heating
Internet
Laundry
8.8
Private Pool
Pool
Oceanfront
EV Charge Station
Hot Tub
Barbecue/Outdoor Cooking
Skiing
