You might be eligible for a Genius discount at Winchester Inn. To check if a Genius discount is available for your selected dates sign in.
Genius discounts at this property are subject to book dates, stay dates and other available deals.
Get the celebrity treatment with world-class service at Winchester Inn
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 ambience. Breakfast includes champagne, fresh pastries, and a variety of warm dishes, highly praised by guests. Convenient Location: Located 38 km from Rogue Valley International-Medford Airport, the hotel is near Oregon Cabaret Theatre (2-minute walk), Ashland Library (300 metres), and Oregon Shakespeare Festival (4-minute walk). An ice-skating rink is also nearby.
Couples particularly like the location — they rated it 9.9 for a two-person trip.
Distance in property description is calculated using © OpenStreetMap
Most popular facilities
- 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 single bed and 1 extra-large double bed | ||
1 single bed and 1 extra-large double bed | ||
Bedroom 1 1 large double bed Bedroom 2 1 extra-large double bed Living room 1 sofa bed | ||
1 sofa bed and 1 large double bed | ||
1 extra-large double bed | ||
Bedroom 1 extra-large double bed Living room 1 sofa bed | ||
Bedroom 1 extra-large double bed Living room 1 sofa bed | ||
1 extra-large double bed | ||
1 sofa bed and 1 large double bed | ||
Bedroom 1 large double bed Living room 1 sofa bed | ||
1 extra-large double bed | ||
1 extra-large double bed | ||
1 large double bed | ||
1 sofa bed and 1 large double bed | ||
1 extra-large double bed | ||
1 large double bed | ||
1 extra-large double bed | ||
1 extra-large double bed and 1 sofa bed | ||
1 extra-large double bed | ||
1 large double bed | ||
1 extra-large double bed and 1 sofa bed |
Guest reviews
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Guests who stayed here loved
- Nischal
Australia
“The staff (in particular Skye) was very friendly and accommodating. The room and bathroom was clean. Skye provided us with chocolates and comp'd the water due to the room and lack of breakfast inconveniences. Location is great with free parking...” - Jean
United States
“Beautiful setting, location centrally located. Staff attentive and kind. Rooms comfortable with great attention to details. Restaurant very comfortable for solo traveler and food was excellent. Will return whenever possible.” - Gohar
United Arab Emirates
“The property is beautiful, it’a nicely decorated, it’s run by the family so the people attending to guests are obviously very capable and committed.” - Heather
United Kingdom
“Quaint property sympathetically decorated. Breakfast excellent” - Ralph
Netherlands
“Nice location, beautiful old building. Excellent food” - Anna-lena
Germany
“Breakfast was excellent! We loved the fresh pastries + choices available from the menu for second course. Centrally located. Very attentive staff. Cute interior.” - Barbara
United States
“Perfect location, beautiful grounds and rooms. Delicious breakfast!” - Peter
Australia
“Beautiful building and rooms-well appointed and comfortable-great styling Very friendly staff-excellent happy hour in the bar and delicious breakfast-thoroughly recommend” - Chris
United States
“Loved the breakfast and all the staff. The bartenders and cocktail menus are incredible.” - Eric
United States
“Excellent 2-course breakfast with coffee and juice. Excellent bar, but it closes by 10pm so its still quiet in near-by rooms for sleeping. Great neighborhood and you can easily walk to theatre venues. Excellent restaurants close-by, as well as...”
Hotel surroundings
Restaurants
- Alchemy Restaurant and Bar
- CuisineAmerican • French • Local • International
- AmbianceModern • Romantic
- Dietary optionsVegetarian • Gluten-free • Dairy-free
- Chateaubriand 36
- CuisineFrench • Steakhouse
- Open forDinner
- AmbianceFamily friendly
House rules
Child policies
Children of any age are welcome.
Children 9 years and above will be charged as adults at this property.
To see correct prices and occupancy information, please add the number of children in your group and their ages to your search.
Cot and extra bed policies
Prices for cots and extra beds are not included in the total price, and will have to be paid for separately during your stay.
The number of extra beds and cots allowed is dependent on the option you choose. Please check your selected option for more information.
All cots and extra beds are subject to availability.




The fine print
Guests are required to show a photo identification 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 in advance of your expected arrival time. You can use the Special Requests box when booking, or contact the property directly with the contact details provided in your confirmation.
In response to Coronavirus (COVID-19), additional safety and sanitation measures are in effect at this property.
A damage deposit of US$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 via credit card, subject to an inspection of the property.