Historic Downtown District Rentals USA Oregon Medford Historic Downtown District

Winchester Inn | Hotel in Ashland, OR

| 9.8 (251 Reviews) |  1 Bathroom
Historic Downtown District Hotel | Winchester Inn

Hotel with Balcony, Fireplace and Guest Services

Victorian inn with free breakfast and a restaurant
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. Additionally, rooms include irons/ironing boards and fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

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35 S. 2nd St., Ashland, 97520, United States

Amenities

Air Conditioner
Parking
TV
Balcony/Terrace
Accessibility
Security/Safety
Business Services
Bedding/Linens
Wellness Facilities
Fireplace/Heating
Restaurant
Bar
Toiletries
Guest Services
Breakfast
Child Friendly
Internet
Kitchen
Laundry

Facility Overview

Bathrooms
  • Towels
  • Hair dryer
  • Designer toiletries
  • Bathrobes
Bedroom
  • Hypo-allergenic bedding
  • Pillow-top mattress
  • Air conditioning
  • Egyptian cotton sheets
  • Fan
  • Premium bedding
  • Down comforter
  • Heating
  • Bed sheets
  • Iron/ironing board
  • Phone
  • Individually decorated
  • Individually furnished
Breakfast
  • 1 restaurant
  • Free cooked-to-order breakfast available daily 8 AM–9:30 AM
  • 1 bar
  • Minibar
  • Coffee/tea maker
  • Electric kettle
Parking
  • Free self parking on site
Accessibility
  • Wheelchair accessible (may have limitations)
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • This property does not have elevators
Entertainment
  • Flat-screen TV
  • Cable channels
General
  • Meeting room
  • Free newspapers in lobby
  • Gift shop/newsstand
  • English
  • Smoke-free property
Guest Services
  • Concierge services
  • Luggage storage
  • Dry cleaning service
  • Tour/ticket assistance
  • Daily housekeeping
  • Front desk (limited hours)
Internet
  • Available in some public areas: Free WiFi
  • Available in all rooms: Free WiFi
Outdoors
  • Terrace
  • Garden

Policies

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
A late check-out fee will be charged check-out before 11 am
Child Policy
Children are welcome. cribs (infant beds) are not available.
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
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 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

Nick
Jul 24, 2025 12:48:18 AM
Review Score:   10
Summary: This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks.
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Room Arrangement

Room Info Facilities
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

Number of living rooms 0, Ping - 9.84, Number of bedrooms - 0, Shower/tub combination, Square feet - 350, Extra bed count 1, Square meters - 33, Number of bathrooms - 1, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Bed count minimum 1, Bed count maximum 1
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, Number of bedrooms - 2, Shower only, Sofa bed, Wheelchair accessible, Number of living rooms 1, Number of bathrooms - 2, 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

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, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Bed count minimum 1, Bed count maximum 1, 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, Number of bedrooms - 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
Suite, 1 King Bed (Fordyce)
Room Size: 450 square feet m2
1 King Bed
Suite, 1 King Bed (Fordyce)

General

Number of living rooms 0, Number of bedrooms - 0, Fireplace, Square feet - 450, Extra bed count 1, Number of bathrooms - 1, Square meters - 42, Jetted bathtub, Private bathroom, Rollaway/extra beds (free), Separate bathtub and shower, Ping - 12.65, Bed count minimum 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

Number of living rooms 0, Ping - 9.84, Number of bedrooms - 1, Shower only, Sofa bed, Square feet - 350, Extra bed count 2, Square meters - 33, Number of bathrooms - 1, Private bathroom, Rollaway/extra beds (free), Bed count minimum 2, 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

Number of living rooms 0, Square feet - 500, Number of bedrooms - 0, Fireplace, Shower/tub combination, Square meters - 46, Extra bed count 1, Number of bathrooms - 1, Jetted bathtub, Private bathroom, Rollaway/extra beds (free), Ping - 14.05, Bed count minimum 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
Double Room, 1 Queen Bed (Catharine M)
Room Size: 300 square feet m2
1 Queen Bed
Double Room, 1 Queen Bed (Catharine M)

General

Number of living rooms 0, Number of bedrooms - 0, Shower/tub combination, Square meters - 28, Square feet - 300, Extra bed count 1, Number of bathrooms - 1, Private bathroom, Rollaway/extra beds (free), Deep soaking bathtub, Bed count minimum 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

Number of living rooms 0, Number of bedrooms - 0, Fireplace, Shower only, Square meters - 37, Square feet - 400, Extra bed count 1, Number of bathrooms - 1, Ping - 11.24, Private bathroom, Rollaway/extra beds (free), Bed count minimum 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 $230 per night with includes Toiletries, Internet, TV, Accessibility, Security/Safety, Business Services, Child Friendly, Laundry, Restaurant, Kitchen, Balcony/Terrace, Fireplace/Heating, Guest Services, Breakfast, Air Conditioner, Parking, Bedding/Linens, Wellness Facilities, Bar 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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