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Winchester Inn

3.5 star property

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Photo gallery for Winchester Inn

Front of property
A modern living room with a sofa, coffee table, and a TV. There is a large window with curtains, a mirror, and a view of a bedroom.
Suite, 1 King Bed (Hargadine) | Bathroom shower
Bar (on property)
Suite, 1 King Bed (Hargadine) | Living room | Flat-screen TV

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free Wi-Fi
  • Air-conditioning
  • Business services

Explore the area

View in a map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Cabaret Theatre
    ‪1 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Place, Allen Elizabethan Theatre
    ‪5 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪23 min drive‬

Room options

View all photos for Double Room, 1 Bedroom (Garden)

Double Room, 1 Bedroom (Garden) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Bedroom (Garden)

10.0 out of 10
Exceptional
(1 review)
  • 33 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Double Room, 1 Bedroom (Sylvan)

Double Room, 1 Bedroom (Sylvan) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Bedroom (Sylvan)

9.6 out of 10
Exceptional
(5 reviews)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room (Queen Anne)

10.0 out of 10
Exceptional
(1 review)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Single Bed
  • Free Wi-Fi

View all photos for Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Queen Bed (Patio)

9.4 out of 10
Exceptional
(3 reviews)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Double Room, 1 Queen Bed (Marjorie Roy)

Double Room, 1 Queen Bed (Marjorie Roy) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Queen Bed (Marjorie Roy)

  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Double Room, 1 Queen Bed (Catharine M)

Double Room, 1 Queen Bed (Catharine M) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Queen Bed (Catharine M)

10.0 out of 10
Exceptional
(5 reviews)
  • 28 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Sunset)

Double Room, 1 King Bed (Sunset) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 King Bed (Sunset)

10.0 out of 10
Exceptional
(2 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Andrew G)

Double Room, 1 King Bed (Andrew G) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 King Bed (Andrew G)

10.0 out of 10
Exceptional
(3 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Peter Benjamin)

Double Room, 1 King Bed (Peter Benjamin) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 King Bed (Peter Benjamin)

  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Eastlake)

Double Room, 1 King Bed (Eastlake) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 King Bed (Eastlake)

10.0 out of 10
Exceptional
(1 review)
  • 33 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Enders)

Double Room, 1 King Bed (Enders) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 King Bed (Enders)

10.0 out of 10
Exceptional
(1 review)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed with Sofa bed (Robert Gordon)

Suite, 1 King Bed with Sofa bed (Robert Gordon) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 King Bed with Sofa bed (Robert Gordon)

7.0 out of 10
Good
(2 reviews)
  • 46 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 2 Bedrooms (Duet Suite)

Suite, 2 Bedrooms (Duet Suite) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 2 Bedrooms (Duet Suite)

  • 65 sq m
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Hargadine)

Suite, 1 King Bed (Hargadine) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 King Bed (Hargadine)

  • 84 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Barbara Howard)

Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 King Bed (Barbara Howard)

  • 46 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Eleanor Rose)

Suite, 1 King Bed (Eleanor Rose) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 King Bed (Eleanor Rose)

9.0 out of 10
Wonderful
(2 reviews)
  • 46 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 Bedroom (Silverdale)

8.0 out of 10
Very good
(1 review)
  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Single Murphy Bed
  • Free Wi-Fi

View all photos for Suite, 1 Queen Bed with Sofa bed (Brighton)

Suite, 1 Queen Bed with Sofa bed (Brighton) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 Queen Bed with Sofa bed (Brighton)

  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 1 Queen Bed with Sofa bed (Courtyard)

Suite, 1 Queen Bed with Sofa bed (Courtyard) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 Queen Bed with Sofa bed (Courtyard)

  • 42 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Fordyce)

Suite, 1 King Bed (Fordyce) | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Suite, 1 King Bed (Fordyce)

10.0 out of 10
Exceptional
(1 review)
  • 42 sq m
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, Garden View

A bedroom with a bed, a grey sofa, a white armchair, a small table, and a fireplace.

Suite, Garden View

  • Garden view
  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Family Suite, City View

A modern living room with a sofa, coffee table, and a TV. There is a large window with curtains, a mirror, and a view of a bedroom.

Family Suite, City View

  • City view
  • 79 sq m
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Single Bed
  • Free Wi-Fi

View all photos for Superior Suite, Mountain View

A hotel room with a bed, a chair, a sofa, a TV, and a lamp.

Superior Suite, Mountain View

  • Mountain view
  • 46 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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About this property

Winchester Inn

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 on-site.
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 duvets and premium bedding. Flat-screen televisions come with cable channels.

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

Our customers tell us that they can't get enough of the helpful staff at Winchester Inn. During your stay, you're just a quick walk from Oregon Shakespeare Festival. Features include free breakfast, free WiFi in public areas and free self-parking.
  • Free cooked-to-order breakfast served daily
  • Free WiFi
  • Free self-parking
  • Grab something to eat at the restaurant or stop for a drink at the bar/lounge
  • Services include dry cleaning/laundry, a concierge and tour or ticket assistance
  • Steps from Oregon Cabaret Theatre and 4 minutes on foot from Oregon Shakespeare Festival
There's a restaurant on site. You can enjoy a drink at the bar/lounge. Free breakfast is available daily. WiFi is free in public spaces.

A terrace, gift shops/newsstands, and tour/ticket assistance are also featured at Winchester Inn. Free self parking is available.

This Victorian Ashland inn is smoke free.

Guests are served a free cooked-to-order breakfast daily from 8 AM to 9:30 AM.
Winchester Inn has a restaurant on site.

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transport

  • Free self parking on site
  • Limited on-site self parking

Food and drink

  • Free cooked-to-order breakfast available daily 8 AM to 9:30 AM
  • A bar/lounge
  • A restaurant

Conveniences

  • Free newspapers in lobby
  • Gift shop/newsstand
  • Limited-hour front desk
  • Luggage storage

Guest services

  • Concierge services
  • Dry cleaning/laundry service
  • Housekeeping (daily)
  • Tour and ticket assistance

Business services

  • Meeting room

Outdoors

  • Garden
  • Terrace

Accessibility

  • Hardwood flooring in room
  • High-pile carpet in room
  • No lift

More

  • 3 floors
  • 5 buildings
  • Built in 1886
  • Smoke-free property
  • Victorian architecture

Room amenities

Bedroom

  • Down comforter
  • Egyptian cotton sheets
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Designer toiletries
  • Dressing gowns
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Connecting rooms available
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop workspace
  • Phone

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

Check-out before 11 AM
A late check-out fee will be charged

Special check-in instructions

The front desk is open daily from 7:30 AM - 8 PM
Front desk staffed during limited hours
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Cots (infant beds) are not available.

Payment types at the property

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • A tax is imposed by the city: USD 9
  • 4 per cent destination fee will be charged.
  • Administrative fee: USD 10.00 per accommodation, per night

We've listed all charges provided to us by the property.

Optional extras

The fees and deposits listed below will be charged at the time of service, check-in, or check-out.

  • A late check-out fee will be charged

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
The front desk at this property is open daily from 7:30 AM - 8 PM.
Front desk staff will greet guests on arrival at the property.

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.
  • Connecting/adjoining rooms are subject to availability and can be requested by contacting the property at the number on your booking confirmation.

Property is also known as

Winchester Inn Ashland
Winchester Ashland
The Winchester Inn
Winchester Inn Inn
Winchester Inn Ashland
Winchester Inn Inn Ashland

Winchester Inn Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 237 out of 275 reviews
Rating 8 - Good. 28 out of 275 reviews
Rating 6 - Okay. 4 out of 275 reviews
Rating 4 - Poor. 3 out of 275 reviews
Rating 2 - Terrible. 3 out of 275 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.6/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Willy

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful B&B. This will now be our favorite stop in Ashland.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Stacey

Liked: Cleanliness, amenities, property conditions & facilities
The room is fantastic!! Highly recommend!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Amy

Liked: Amenities, property conditions & facilities
Loved our stay so much!
Stayed 2 nights in Feb 2025
Verified

10/10 Excellent

Carolyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful room with comfortable bed. Nice quality bedding.
Stayed 1 night in Oct 2025
Verified

10/10 Excellent

Anita

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place to stay
Stayed 1 night in Nov 2023
Verified

10/10 Excellent

Dirk

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, really comfortable bed, pillows and sheets!
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Heather

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful location, friendly staff, amazing stay!
Stayed 1 night in May 2023
Verified

8/10 Good

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was beautiful. Room was large, clean and nicely appointed. The only disappointment was not getting to sample the highly rated breakfast as we learned after we made our booking that the kitchen and restaurant were shut down for a yearly deep clean.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Chris

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always a beautiful place to stay!
Stayed 1 night in Oct 2022
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved everything about this inn!
Stayed 1 night in Apr 2024
Verified

10/10 Excellent

Christi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a unique Victorian place! So charming, clean and spacious….
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Paula

Liked: Cleanliness, staff & service, property conditions & facilities
This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Lovely room
Stayed 1 night in Oct 2025
Verified

8/10 Good

Bradley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff and really clean and comfortable rooms.Love the location and quick walk to local cafe’s and restaurants.
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome location and amazing included breakfast. The bed was cozy and Eastlake room was delightful.
Stayed 2 nights in Oct 2024
Verified

2/10 Terrible

Mei

Disliked: Cleanliness, amenities, property conditions & facilities
Why it calls itself hotel really puzzles me. Very dated dirty carpet, loud split heating/ac, not to mention nobody checks you in at 11pm with poor instructions. Will NEVER stay here.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Charlotte

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved our stay as always. Breakfast was also delicious.
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Ellen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was amazing!
Stayed 1 night in Dec 2023
Verified

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
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.
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent satff that made our stay a pleasure.
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

Aaron

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exceptionally friendly and helpful staff; room was beautiful and clean; one block from many restaurants and shopping.
Verified

10/10 Excellent

Kathleen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!!
Stayed 1 night in Feb 2025
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the restaurant!
Stayed 1 night in Mar 2022