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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 9.9 for a two-person trip.

Distance in property description is calculated using © OpenStreetMap

Property highlights

    • Top Location: Highly rated by recent guests (9.9)

    • Breakfast Info

    • Full English/Irish, American, Breakfast to go

    • Free private parking available at the hotel


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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
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Guest reviews

Categories:

Staff
Facilities
Cleanliness
Comfort
Value for money
Location
Free Wifi

Select topics to read reviews:

Guests who stayed here loved

  • 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!
  • Kris
    United States United States
    The staff see to every detail. We felt as though we were living in luxury! Location was perfect and the grounds are beautiful.
  • Miriam
    United States United States
    We love this inn & have stayed there many times. The staff is wonderful & food exceptional.
  • Peter
    United States United States
    Central location with easy access to OSF theaters. Very comfortable room, lovely breakfast. Would stay here again.
  • Bridget
    United States United States
    Beautiful property, charming room, great location, tasty made-to-order (not a buffet!) breakfast. Easy and safe parking.
  • Anna
    United States United States
    The room was beautiful (bright and spacious and great location) and the breakfast is far beyond what any normal breakfast at a hotel is.
  • Grafiada
    United States United States
    This was the most beautiful hotel! The owners and staff paid attention to elevate every detail.
  • Carola
    United States United States
    enjoyed sitting in the bar and having delicious drinks and a light dinner
  • Scardino
    United States United States
    The staff was very friendly getting us checked in and situated in our room. They were helpful pointing to a good restaurant as it was Monday and many restaurants are closed, including theirs. The breakfast was wonderful…made me wish we had an...

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
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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.

FAQs about Winchester Inn