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About this property
Historic Charm: Winchester Inn in Ashland offers a historic setting with a beautiful garden, tennis court, and free WiFi. The property features a modern restaurant and bar, ideal for relaxation and dining. Comfortable Accommodations: Rooms include air-conditioning, private bathrooms, and amenities such as bathrobes and free toiletries. Family rooms and ground-floor units provide additional comfort, ensuring a pleasant stay for all guests. Dining Experience: The restaurant serves French, American, and local cuisines in a family-friendly, modern, and romantic ambiance. Breakfast includes champagne, fresh pastries, and a variety of warm dishes, highly praised by guests. Convenient Location: Located 24 mi from Rogue Valley International-Medford Airport, the hotel is near Oregon Cabaret Theater (2-minute walk), Ashland Library (984 feet), and Oregon Shakespeare Festival (4-minute walk). An ice-skating rink is also nearby.
Couples in particular like the location – they rated it 9.8 for a two-person trip.
Distance in property description is calculated using © OpenStreetMap
Most popular amenities
- Free parking
- Free Wifi
- Non-smoking rooms
- 2 restaurants
- Facilities for disabled guests
- Family rooms
- Tea/Coffee Maker in All Rooms
- Bar
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Availability
Select dates to see this property's availability and prices
Room Type | Number of guests | |
---|---|---|
1 twin bed and 1 king bed | ||
1 twin bed and 1 king bed | ||
Bedroom 1 1 queen bed Bedroom 2 1 king bed Living room 1 sofa bed | ||
1 sofa bed and 1 queen bed | ||
1 king bed | ||
Bedroom 1 king bed Living room 1 sofa bed | ||
Bedroom 1 king bed Living room 1 sofa bed | ||
1 king bed | ||
1 sofa bed and 1 queen bed | ||
Bedroom 1 queen bed Living room 1 sofa bed | ||
1 king bed | ||
1 king bed | ||
1 queen bed | ||
1 sofa bed and 1 queen bed | ||
1 king bed | ||
1 queen bed | ||
1 king bed | ||
1 king bed and 1 sofa bed | ||
1 king bed | ||
1 queen bed | ||
1 king bed and 1 sofa bed |
Guest reviews
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Guests who stayed here loved
- John
United States
“Great location close to restaurants and shops as well as Lithia Park. The breakfast was delicious. Wonderful server and staff. Clean room with comfortable bed.” - Diane
United States
“Location is ideal. Friendly staff. Food is amazing!” - Theresa
United States
“Our stay here was a huge surprise! What started as just a place to stay while traveling to a mini get-a-way! The entire property was very special from the grounds, to the restaurant, to our room. The staff was really welcoming. There was...” - Adrienne
United States
“Beautiful property with clean rooms. Location is very convenient to the theaters. Staff was stellar.” - Patric
Mexico
“Charming, comfortable, well-appointed, friendly and helpful staff, very convenient to Shakespeare Festival theaters.” - Marlene
United States
“Friendly competent staff, exceedingly comfortable bed and well appointed room, location” - Joan
United States
“The breakfast was fabulous , service with a smile, and a deer grazing outside. Booking.com price was really a discount!” - Jill
United States
“The inn is beautiful, well decorated and welcoming. Its perfectly situated in the heart of Ashland for dining, shopping or theater going.” - June
United States
“The staff was very friendly and professional! The food was spectacular.” - Leslie
United States
“The breakfast was absolutely fantastic! The bathroom with all the products, the lush sheets and balcony, in room coffee - all were wonderful. Thank you!”
Hotel area info
Restaurants
- Alchemy Restaurant and Bar
- CuisineAmerican • French • Local • International
- AmbienceModern • Romantic
- Dietary optionsVegetarian • Gluten-free • Dairy-free
- Chateaubriand 36
- CuisineFrench • Steakhouse
- Open forDinner
- AmbienceFamily-friendly
House rules
Child policies
Children of all ages are welcome.
Children 9 and above will be charged as adults at this property.
To see correct prices and occupancy info, add the number and ages of children in your group to your search.
Crib and extra bed policies
Prices for cribs and extra beds aren't included in the total price. They'll have to be paid for separately during your stay.
The number of extra beds and cribs allowed depends on the option you choose. Check your selected option for more info.
All cribs and extra beds are subject to availability.




The fine print
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 Winchester Inn 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.
In response to the coronavirus (COVID-19), additional safety and sanitation measures are in effect at this property.
A damage deposit of $250 is required on arrival. This will be collected by credit card. You should be reimbursed on check-out. Your deposit will be refunded in full by credit card, subject to an inspection of the property.