You might be eligible for a Genius discount at Winchester Inn. Sign in to check if a Genius discount is available for your selected dates.

Genius discounts at this property are subject to booking dates, stay dates, and other available deals.

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

Property highlights

Top Location: Highly rated by recent guests (9.8)

Breakfast Info

Full English/Irish, American, Breakfast to go

  • Free private parking available at the hotel


Sign in, save money

Sign in to see if you can save 10% or more at this property.
Sign in, save money

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
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.
Something went wrong – please try again later.

Guest reviews

Categories:

Staff
Facilities
Cleanliness
Comfort
Value for money
Location
Free Wifi

Select topics to read reviews:

Guests who stayed here loved

  • John
    United States 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 United States
    Location is ideal. Friendly staff. Food is amazing!
  • Theresa
    United States 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 United States
    Beautiful property with clean rooms. Location is very convenient to the theaters. Staff was stellar.
  • Patric
    Mexico Mexico
    Charming, comfortable, well-appointed, friendly and helpful staff, very convenient to Shakespeare Festival theaters.
  • Marlene
    United States United States
    Friendly competent staff, exceedingly comfortable bed and well appointed room, location
  • Joan
    United States 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 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 United States
    The staff was very friendly and professional! The food was spectacular.
  • Leslie
    United States 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

2 Restaurants On Site
  • Alchemy Restaurant and Bar
    • Cuisine
      American • French • Local • International
    • Ambience
      Modern • Romantic
    • Dietary options
      Vegetarian • Gluten-free • Dairy-free
  • Chateaubriand 36
    • Cuisine
      French • Steakhouse
    • Open for
      Dinner
    • Ambience
      Family-friendly

House rules

Winchester Inn takes special requests – add in the next step!
Check-in
From 4:00 PM
Guests are required to show a photo ID and credit card at check-in.
You need to let the property know what time you'll be arriving in advance.
Check-out
Until 11:00 AM
Cancellation/ prepayment
Cancellation and prepayment policies vary according to accommodation type. Enter your stay dates and check the conditions of your selected option.
Refundable damage deposit
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.
Children & Beds

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

0 - 2 years
Extra bed upon request
Free
Crib upon request
Free
3 - 8 years
Extra bed upon request
Free
9+ years
Extra bed upon request
$45 per person, per night

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.

No age restriction
There's no age requirement for check-in
Pets
Pets are not allowed.
Cards accepted at this hotel
American ExpressVisaMastercardDiscover

The fine print

Must-know information for guests at this property

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.