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Winchester Inn

3.5 star property

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Photo gallery for Winchester Inn

Bar (on property)
Front of property
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area | Flat-screen TV
Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Suite, 1 Bedroom (Silverdale) | Living area | Flat-screen TV

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
$211
includes taxes & fees
Jan 4 - Jan 5, 2026

Explore the area

View in a map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Cabaret Theatre
    ‪1 min walk‬
  • Place, Allen Elizabethan Theatre
    ‪3 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪21 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
  • 1 bedroom
  • 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
  • 2 bedrooms
  • 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
  • Limited onsite self parking

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 9.0
  • 3 percent destination fee will be charged
  • Administrative fee: USD 6.00 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
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

9.8

Exceptional

Rating 10 - Excellent. 227 out of 263 reviews
Rating 8 - Good. 27 out of 263 reviews
Rating 6 - Okay. 4 out of 263 reviews
Rating 4 - Poor. 3 out of 263 reviews
Rating 2 - Terrible. 2 out of 263 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.4/10

Eco-friendliness

Reviews

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

10/10 Excellent

Len

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention.
Stayed 2 nights in May 2025

10/10 Excellent

Thomas

Stayed 1 night in Mar 2025

10/10 Excellent

Verified traveler

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

10/10 Excellent

Raul

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 3 nights in Mar 2025

10/10 Excellent

Amy

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

10/10 Excellent

Kathleen

Business traveler
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

10/10 Excellent

Leonilda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great and beautiful place to stay. Delicious brea

Stayed 1 night in Jan 2025

10/10 Excellent

Donna

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jan 2025

10/10 Excellent

Diana

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Wonderful

The Winchester, especially the Hargadine Suite, is the best hotel on the west coast. I love it so much it is a very very uniquely special place. I go to Ashland specifically for the Winchester and their amazing breakfast.
Stayed 2 nights in Jan 2025

10/10 Excellent

Leonilda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Beautiful and unique

Stayed 1 night in Dec 2024

10/10 Excellent

Leonilda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Friendly, comfortable & unique place to enjoy

Great beautiful Inn with unique rooms. Delicious breakfast nenu with gluten-free items that are wonderful and I so enjoy
Stayed 1 night in Jan 2025

10/10 Excellent

Monica

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.
Stayed 2 nights in Jan 2025

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Dec 2024

8/10 Good

Rebecca A

Business traveler, Traveled with family
Liked: Staff & service, property conditions & facilities, room comfort

Great place, but.....

The place and staff is fabulous. Always like it. Sorry to say I have the same complaint now as last time we were there, and we stayed in a different room. The carpets were filthy. Even if they were clean, they looked horrible with all the stains. How about hard wood floors or..... Thanks for listening.
Stayed 1 night in Dec 2024

4/10 Poor

Anna

Disliked: Property conditions & facilities, room comfort
Stayed 4 nights in Dec 2024

10/10 Excellent

Rob

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!
Stayed 1 night in Nov 2024

10/10 Excellent

Robin

Traveled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely hotel in downtown Ashland. High end restaurant attached with lovely bar, as well as outdoor seating options. Walkable to all things in downtown. Stairs required up to room. Large comfortable room. Very nice breakfast. Overall, hotel is expensive, but nice. We really enjoy the restaurant.
Stayed 1 night in Sep 2024