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Winchester Inn

3.5 star property

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Photo gallery for Winchester Inn

Front of property
Suite, 2 Bedrooms (Duet Suite) | Living area | Flat-screen TV
Suite, 1 King Bed (Hargadine) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
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 WiFi
  • Air conditioning
  • Business services
The current price is $366
includes taxes & fees
May 24 - May 25

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, Lithia Park
    ‪3 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 comforters, pillowtop beds

Double Room, 1 Bedroom (Garden)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Bedroom (Sylvan) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Bedroom (Sylvan)

9.6 out of 10
Exceptional
(5 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room (Queen Anne)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Bed

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

Double Room, 1 Queen Bed (Patio) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Patio)

9.4 out of 10
Exceptional
(3 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Queen Bed (Marjorie Roy) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Marjorie Roy)

  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Queen Bed (Catharine M) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Catharine M)

10.0 out of 10
Exceptional
(5 reviews)
  • 300 sq ft
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 King Bed (Sunset) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Sunset)

10.0 out of 10
Exceptional
(2 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 King Bed (Andrew G) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Andrew G)

10.0 out of 10
Exceptional
(3 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 King Bed (Peter Benjamin) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Peter Benjamin)

  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 King Bed (Eastlake) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Eastlake)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 King Bed (Enders) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Enders)

10.0 out of 10
Exceptional
(1 review)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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 comforters, pillowtop beds

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

7.0 out of 10
Good
(2 reviews)
  • 500 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed and 1 Double Sofa Bed

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

Suite, 2 Bedrooms (Duet Suite) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 2 Bedrooms (Duet Suite)

  • 700 sq ft
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed

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

Suite, 1 King Bed (Hargadine) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Hargadine)

  • 900 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Barbara Howard)

  • 500 sq ft
  • Sleeps 2
  • 1 King Bed

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

Suite, 1 King Bed (Eleanor Rose) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Eleanor Rose)

9.0 out of 10
Wonderful
(2 reviews)
  • 500 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 Bedroom (Silverdale)

8.0 out of 10
Very good
(1 review)
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Murphy Bed

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 comforters, pillowtop beds

Suite, 1 Queen Bed with Sofa bed (Brighton)

  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

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 comforters, pillowtop beds

Suite, 1 Queen Bed with Sofa bed (Courtyard)

  • 450 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

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

Suite, 1 King Bed (Fordyce) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Fordyce)

10.0 out of 10
Exceptional
(1 review)
  • 450 sq ft
  • Sleeps 2
  • 1 King Bed

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About this property

Winchester Inn

3.5-star inn in Historic Downtown District
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.

The inn offers a restaurant. A bar/lounge is on site where guests can unwind with a drink. Guests can enjoy a complimentary breakfast each morning. Public areas are equipped with complimentary wireless Internet access.

This Victorian inn also offers a terrace, gift shops/newsstands, and tour/ticket assistance. Complimentary self parking is available on site.

Winchester Inn is a smoke-free property.

A complimentary cooked-to-order breakfast is served each morning between 8 AM and 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 transportation

  • Free self parking on site

Food and drink

  • Free cooked-to-order breakfast available daily 8:00 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator
  • Wheelchair accessible (may have limitations)

More

  • 3 floors
  • 5 buildings
  • Built in 1886
  • Smoking not allowed
  • Victorian architecture

Room amenities

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Fan
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • 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

Pets not allowed

Children and extra beds

Children are welcome

Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

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

We have included all charges provided to us by the property.

Optional extras

  • 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.

You need to know

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, 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

We should mention

This property does not have elevators
Only registered guests are allowed in the guestrooms

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

10/10 Excellent

Stacey

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

2/10 Terrible

Mei, Sunnyvale

Traveled with group
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

8/10 Good

James

Traveled with partner
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

10/10 Excellent

Jill

Stayed 1 night in Nov 2025

10/10 Excellent

Jack

Stayed 1 night in Dec 2025

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

10/10 Excellent

Ann

Stayed 1 night in Nov 2025

10/10 Excellent

Marcia

Stayed 1 night in Nov 2025

10/10 Excellent

JOHN AND NANCY

Stayed 1 night in Dec 2025

10/10 Excellent

Marcia

Stayed 1 night in Nov 2025

10/10 Excellent

Gloria

Stayed 1 night in Nov 2025

10/10 Excellent

David

Stayed 1 night in Nov 2025

6/10 Okay

Richard

Stayed 1 night in Oct 2025

10/10 Excellent

Carolyn

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

10/10 Excellent

Robert

Stayed 1 night in Sep 2025

10/10 Excellent

Patricia

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

10/10 Excellent

Joe

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

10/10 Excellent

Laura

Traveled with partner
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

10/10 Excellent

Shanna

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.
Stayed 2 nights in Sep 2025

10/10 Excellent

Christi

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

10/10 Excellent

Bette, Eugene

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful setting with great service and food. Only problem was the bees nest above our patio room. Couldn’t sit outside because of the bees.
Stayed 2 nights in Aug 2025

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

10/10 Excellent

Heather

Weekend getaway

The room was amazing, and perfect location . The only negative was how small the tv was but we didn’t end up using it do wasn’t a big deal. The fire place motor sounded like it was on when everything was turned off. The room was amazing and definitely will come back, breakfast was good only bummer was the expresso machine was broken. The bed was comfortable, and staff was great. I love the little touch and personalization in the room.
Stayed 1 night in Jul 2025

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

8/10 Good

Sid

Traveled with family
Liked: Cleanliness
The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.
Stayed 2 nights in Jun 2025