Historic Downtown District Rentals USA Oregon Medford Historic Downtown District

Winchester Inn | Hotel in Ashland, OR

| 9.6 (275 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
AccessibilityAccessibility
Security/SafetySecurity/Safety
Business ServicesBusiness Services
Bedding/LinensBedding/Linens
Wellness FacilitiesWellness Facilities
Fireplace/HeatingFireplace/Heating
RestaurantRestaurant
BarBar
ToiletriesToiletries
Guest ServicesGuest Services
BreakfastBreakfast
Child FriendlyChild Friendly
InternetInternet
KitchenKitchen
LaundryLaundry

Facility Overview

BathroomsBathrooms
  • BathrobesBathrobes
  • SoapSoap
  • Designer toiletriesDesigner toiletries
  • Toilet paperToilet paper
  • ShampooShampoo
  • Hair dryerHair dryer
  • TowelsTowels
BedroomBedroom
  • Premium beddingPremium bedding
  • Egyptian cotton sheetsEgyptian cotton sheets
  • Hypo-allergenic beddingHypo-allergenic bedding
  • Air conditioningAir conditioning
  • HeatingHeating
  • Pillow-top mattressPillow-top mattress
  • Down comforterDown comforter
  • Bed sheetsBed sheets
  • Individually decoratedIndividually decorated
  • PhonePhone
  • Connecting rooms availableConnecting rooms available
  • Iron/ironing boardIron/ironing board
  • Laptop-friendly workspaceLaptop-friendly workspace
  • Individually furnishedIndividually furnished
BreakfastBreakfast
  • 1 restaurant1 restaurant
  • 1 bar1 bar
  • Free cooked-to-order breakfast available daily 8 AM–9:30 AMFree cooked-to-order breakfast available daily 8 AM–9:30 AM
  • MinibarMinibar
  • Electric kettleElectric kettle
  • Coffee/tea makerCoffee/tea maker
ParkingParking
  • Free self parking on siteFree self parking on site
AccessibilityAccessibility
  • Hardwood flooring in roomHardwood flooring in room
  • This property does not have elevatorsThis property does not have elevators
  • High pile carpet in roomHigh pile carpet in room
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
EntertainmentEntertainment
  • Flat-screen TVFlat-screen TV
  • Cable channelsCable channels
GeneralGeneral
  • Meeting roomMeeting room
  • Free newspapers in lobbyFree newspapers in lobby
  • Gift shop/newsstandGift shop/newsstand
  • EnglishEnglish
  • Smoke-free propertySmoke-free property
Guest ServicesGuest Services
  • Front desk (limited hours)Front desk (limited hours)
  • Luggage storageLuggage storage
  • Concierge servicesConcierge services
  • Tour/ticket assistanceTour/ticket assistance
  • Dry cleaning serviceDry cleaning service
  • Daily housekeepingDaily housekeeping
InternetInternet
  • Available in all rooms: Free WiFiAvailable in all rooms: Free WiFi
  • Available in some public areas: Free WiFiAvailable in some public areas: Free WiFi
OutdoorsOutdoors
  • GardenGarden
  • TerraceTerrace

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

Damon
Apr 28, 2026 12:29:32 PM
Review Score:   10
Summary: Fabulous breakfast and a great room. Location is right in town, can't really get a better location for the theatres and downtown restaurants. I stay here often.
See All Reviews

Room Arrangement

Room InfoFacilities
Family Suite, City View
Room Size: 850 square feet m2
3 King Bed, Queen Bed and Twin Bed
Family Suite, City View

General

Number of bedrooms - 2, Shower only, Ping - 24, Square feet - 850, Square meters - 79, Wheelchair accessible, Extra bed count 1, Number of living rooms 1, Number of bathrooms - 1, Furnished patio, Private bathroom, Rollaway/extra beds (free), Separate sitting area, Bed count maximum 3, Access via exterior corridors, City view, Bed count minimum 3
Suite, 1 King Bed (Hargadine)
Room Size: 900 square feet m2
1 King Bed
Suite, 1 King Bed (Hargadine)

General

Ping - 25.29, Fireplace, Square feet - 900, Number of bedrooms - 1, Separate bedroom, Extra bed count 1, Number of living rooms 1, Number of bathrooms - 1, Jetted bathtub, Square meters - 84, Private bathroom, Rollaway/extra beds (free), Separate bathtub and shower, Separate sitting area, Rainfall showerhead, Bed count minimum 1, Bed count maximum 1, Furnished balcony
Double Room, 1 Queen Bed (Patio)
Room Size: 350 square feet m2
1 Queen Bed
Double Room, 1 Queen Bed (Patio)

General

Number of living rooms 0, Ping - 9.84, Number of bedrooms - 0, Shower only, Square feet - 350, Extra bed count 1, Square meters - 33, Number of bathrooms - 1, Balcony or patio, Furnished patio, Private bathroom, Rollaway/extra beds (free), Access via exterior corridors, Bed count minimum 1, Bed count maximum 1
Double Room, 1 Queen Bed (Marjorie Roy)
Room Size: 350 square feet m2
1 Queen Bed
Double Room, 1 Queen Bed (Marjorie Roy)

General

Private bathroom, Rollaway/extra beds (free), Ping - 9.84, Deep soaking bathtub, Shower/tub combination, Square feet - 350, Bed count minimum 1, Extra bed count 1, Bed count maximum 1, Square meters - 33
Double Room, 1 Bedroom (Garden)
Room Size: 350 square feet m2
1 Queen Bed
Double Room, 1 Bedroom (Garden)

General

Number of living rooms 0, Private bathroom, Rollaway/extra beds (free), Ping - 9.84, Number of bedrooms - 1, Shower only, Square feet - 350, Bed count minimum 1, Extra bed count 1, Bed count maximum 1, Square meters - 33, Number of bathrooms - 1
Suite, 1 King Bed (Barbara Howard)
Room Size: 500 square feet m2
1 King Bed
Suite, 1 King Bed (Barbara Howard)

General

Number of living rooms 0, Square feet - 500, Number of bedrooms - 0, Fireplace, Ping - 14, Square meters - 46, Extra bed count 1, Number of bathrooms - 1, Jetted bathtub, Private bathroom, Rollaway/extra beds (free), Separate bathtub and shower, Bed count minimum 1, Bed count maximum 1
Suite, 1 King Bed with Sofa bed (Robert Gordon)
Room Size: 500 square feet m2
2 King Bed and Double Sofa Bed
Suite, 1 King Bed with Sofa bed (Robert Gordon)

General

Square feet - 500, Fireplace, Shower/tub combination, Number of bedrooms - 1, Sofa bed, Separate bedroom, Square meters - 46, Number of living rooms 1, Extra bed count 2, Number of bathrooms - 1, Jetted bathtub, Private bathroom, Rollaway/extra beds (free), Ping - 14.05, Separate sitting area, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Double Room (Queen Anne)
Room Size: 350 square feet m2
2 Queen Bed and Twin Bed
Double Room (Queen Anne)

General

Number of living rooms 0, Private bathroom, Rollaway/extra beds (free), Ping - 9.84, Number of bedrooms - 0, Shower only, Square feet - 350, Extra bed count 1, Bed count minimum 2, Square meters - 33, Number of bathrooms - 1, Bed count maximum 2
Suite, 2 Bedrooms (Duet Suite)
Room Size: 700 square feet m2
3 King Bed, Queen Bed and Double Sofa Bed
Suite, 2 Bedrooms (Duet Suite)

General

Square feet - 700, Shower only, Sofa bed, Wheelchair accessible, Ping - 20, Extra bed count 2, Square meters - 65, Furnished patio, Private bathroom, Rollaway/extra beds (free), Separate sitting area, Bed count maximum 3, Access via exterior corridors, Bed count minimum 3
Double Room, 1 King Bed (Andrew G)
Room Size: 400 square feet m2
1 King Bed
Double Room, 1 King Bed (Andrew G)

General

Ping - 11.24, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Shower/tub combination, Sofa bed, Square meters - 37, Square feet - 400, Bed count minimum 1, Bed count maximum 1, Extra bed count 2, Furnished balcony
Suite, 1 Queen Bed with Sofa bed (Courtyard)
Room Size: 450 square feet m2
2 Queen Bed and Double Sofa Bed
Suite, 1 Queen Bed with Sofa bed (Courtyard)

General

Number of living rooms 0, Square feet - 450, Sofa bed, Ping - 13, Extra bed count 2, Number of bathrooms - 1, Square meters - 42, Jetted bathtub, Furnished patio, Private bathroom, Rollaway/extra beds (free), Separate bathtub and shower, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Double Room, 1 King Bed (Eastlake)
Room Size: 350 square feet m2
1 King Bed
Double Room, 1 King Bed (Eastlake)

General

Number of living rooms 0, Ping - 9.84, Number of bedrooms - 0, Shower only, Square feet - 350, Extra bed count 1, Square meters - 33, Number of bathrooms - 1, Private bathroom, Rollaway/extra beds (free), Access via exterior corridors, Bed count minimum 1, Bed count maximum 1
Double Room, 1 King Bed (Peter Benjamin)
Room Size: 400 square feet m2
1 King Bed
Double Room, 1 King Bed (Peter Benjamin)

General

Number of living rooms 0, Number of bedrooms - 0, Shower/tub combination, Sofa bed, Square meters - 37, Square feet - 400, Extra bed count 2, Number of bathrooms - 1, Ping - 11.24, Furnished patio, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Bed count minimum 1, Bed count maximum 1
Superior Suite, Mountain View
Room Size: 500 square feet m2
2 King Bed and Double Sofa Bed
Superior Suite, Mountain View

General

Square feet - 500, Number of bedrooms - 1, Shower only, Ping - 14, Square meters - 46, Mountain view, Extra bed count 1, Number of living rooms 1, Number of bathrooms - 1, Private bathroom, Rollaway/extra beds (free), Separate sitting area, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Suite, 1 King Bed (Fordyce)
Room Size: 450 square feet m2
1 King Bed
Suite, 1 King Bed (Fordyce)

General

Square meters - 42, Jetted bathtub, Private bathroom, Rollaway/extra beds (free), Separate bathtub and shower, Fireplace, Ping - 12.65, Square feet - 450, Bed count minimum 1, Extra bed count 1, Bed count maximum 1
Double Room, 1 King Bed (Enders)
Room Size: 400 square feet m2
1 King Bed
Double Room, 1 King Bed (Enders)

General

Number of living rooms 0, Number of bedrooms - 0, Shower/tub combination, Square meters - 37, Square feet - 400, Extra bed count 1, Number of bathrooms - 1, Ping - 11.24, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Access via exterior corridors, Bed count minimum 1, Bed count maximum 1
Double Room, 1 Bedroom (Sylvan)
Room Size: 350 square feet m2
2 Queen Bed and Double Sofa Bed
Double Room, 1 Bedroom (Sylvan)

General

Private bathroom, Rollaway/extra beds (free), Ping - 9.84, Shower only, Sofa bed, Square feet - 350, Bed count minimum 2, Extra bed count 2, Square meters - 33, Bed count maximum 2
Suite, 1 King Bed (Eleanor Rose)
Room Size: 500 square feet m2
1 King Bed
Suite, 1 King Bed (Eleanor Rose)

General

Jetted bathtub, Square feet - 500, Private bathroom, Rollaway/extra beds (free), Ping - 14.05, Fireplace, Shower/tub combination, Square meters - 46, Bed count minimum 1, Extra bed count 1, Bed count maximum 1
Suite, 1 Bedroom (Silverdale)
Room Size: 450 square feet m2
2 Queen Bed and Twin Murphy Bed
Suite, 1 Bedroom (Silverdale)

General

Fireplace, Number of bedrooms - 1, Square feet - 450, Sofa bed, Separate bedroom, Number of living rooms 1, Extra bed count 2, Number of bathrooms - 1, Square meters - 42, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Separate bathtub and shower, Ping - 12.65, Separate sitting area, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Suite, 1 Queen Bed with Sofa bed (Brighton)
Room Size: 450 square feet m2
2 Queen Bed and Double Sofa Bed
Suite, 1 Queen Bed with Sofa bed (Brighton)

General

Fireplace, Number of bedrooms - 1, Square feet - 450, Shower only, Sofa bed, Separate bedroom, Number of living rooms 1, Extra bed count 2, Number of bathrooms - 1, Square meters - 42, Private bathroom, Rollaway/extra beds (free), Ping - 12.65, Separate sitting area, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Suite, Garden View
Room Size: 450 square feet m2
2 Queen Bed and Double Sofa Bed
Suite, Garden View

General

Number of living rooms 0, Fireplace, Number of bedrooms - 1, Square feet - 450, Laptop-friendly workspace, Extra bed count 1, Number of bathrooms - 1, Square meters - 42, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Separate bathtub and shower, Ping - 12.65, Garden view, Separate sitting area, Access via exterior corridors, Bed count minimum 2, Bed count maximum 2
Double Room, 1 Queen Bed (Catharine M)
Room Size: 300 square feet m2
1 Queen Bed
Double Room, 1 Queen Bed (Catharine M)

General

Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Shower/tub combination, Square meters - 28, Square feet - 300, Bed count minimum 1, Extra bed count 1, Bed count maximum 1, Ping - 8.43
Double Room, 1 King Bed (Sunset)
Room Size: 400 square feet m2
1 King Bed
Double Room, 1 King Bed (Sunset)

General

Ping - 11.24, Private bathroom, Rollaway/extra beds (free), Fireplace, Shower only, Square meters - 37, Square feet - 400, Bed count minimum 1, Extra bed count 1, Bed count maximum 1, Furnished balcony

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 $403 per night with includes Business Services, Fireplace/Heating, Bar, Breakfast, Accessibility, Guest Services, Parking, Security/Safety, Wellness Facilities, Child Friendly, Internet, Laundry, Air Conditioner, TV, Balcony/Terrace, Bedding/Linens, Restaurant, Toiletries, Kitchen with all other facilities. Casai.co.za 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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