Winchester Inn | Hotel in Ashland, OR

| 9.6 (289 Reviews) |  1 Bathroom
Historic Downtown District Hotel | Winchester Inn

Hotel with Air Conditioner, Parking and TV

Along with a restaurant, this smoke-free inn has a bar/lounge and a meeting room. Free cooked-to-order breakfast, free WiFi in public areas, and free self parking are also provided. Additionally, concierge services, dry cleaning, and free newspapers are onsite.
Winchester Inn offers 21 air-conditioned accommodations with minibars and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

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35 S. 2nd St., Ashland, 97520, USA

Amenities

Air ConditionerAir Conditioner
ParkingParking
TVTV
Balcony/TerraceBalcony/Terrace
Security/SafetySecurity/Safety
Business ServicesBusiness Services
Bedding/LinensBedding/Linens
Wellness FacilitiesWellness Facilities
RestaurantRestaurant
BarBar
ToiletriesToiletries
Guest ServicesGuest Services
BreakfastBreakfast
Child FriendlyChild Friendly
HeatingHeating
InternetInternet
KitchenKitchen
LaundryLaundry

Policies

Check-in
Check-in
Check-in start time: 4:00 pm; check-in end time: 9 pm late check-in subject to availability minimum check-in age: 21
Check-out
Check-out
A late check-out fee will be charged check-out before 11 am
Child Policy
Child Policy
Children are welcome. cribs (infant beds) are not available.
Payment Policy
Payment Policy
A late check-out fee will be charged the above list may not be comprehensive. fees and deposits may not include tax and are subject to change.
Pet Policy
Pet Policy
Pets not allowed
Extra-person charges may apply and vary depending on property policy government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges safety features at this property include a fire extinguisher special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed this property accepts credit cards; cash is not accepted this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

Reviews

James
Jul 13, 2026 10:28:29 PM
Review Score:   10
Summary: The room was perfect. A comfortable Victorian room and house close to the downtown Ashland events. The two course breakfast was wonderful and not rushed. Take your time to enjoy the place and your stay in Ashland. One note, parking is available onsite if you don’t want to park on the streets, but is tricky to find. Go around the back from the south side for the lot. We also had dinner across the street at Chateaubriand: amazing French cuisine.
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FAQ's

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.

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.

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, TV, Balcony/Terrace, Security/Safety, Business Services, Bedding/Linens, Wellness Facilities, Restaurant, Bar, Toiletries, Guest Services, Breakfast, Child Friendly, Heating, Internet, Kitchen, Laundry with all other facilities. Casai.ca matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

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 3 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.

Is the Winchester Inn wheelchair accessible or offer services for disabled guests? 

Based on the information received from our partner, the Winchester Inn has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

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.

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: Cancellation Policy 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.

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