See all properties
Save

Winchester Inn

3.5 star property

Photo gallery for Winchester Inn

Front of property
Bar (on property)
Suite, 1 King Bed (Hargadine)
Suite, 2 Bedrooms (Duet Suite) | Living area
Suite, 1 King Bed (Hargadine) | Living room

Reviews

9.6 out of 10
Exceptional

Popular amenities

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

Explore the area

View map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Cabaret Theatre
    ‪1 min walk‬
  • Place, Thomas 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)

Double Room, 1 Bedroom (Garden)

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

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

Double Room, 1 Bedroom (Sylvan)

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

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

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

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

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio)

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

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

Double Room, 1 Queen Bed (Marjorie Roy)

Double Room, 1 Queen Bed (Marjorie Roy)

  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Queen Bed (Catharine M)

Double Room, 1 Queen Bed (Catharine M)

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

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

Double Room, 1 King Bed (Sunset)

Double Room, 1 King Bed (Sunset)

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

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

Double Room, 1 King Bed (Andrew G)

Double Room, 1 King Bed (Andrew G)

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

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

Double Room, 1 King Bed (Peter Benjamin)

Double Room, 1 King Bed (Peter Benjamin)

  • 37 sq m
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 King Bed (Eastlake)

Double Room, 1 King Bed (Eastlake)

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

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

Double Room, 1 King Bed (Enders)

Double Room, 1 King Bed (Enders)

10.0 out of 10
Exceptional
(1 review)
  • 37 sq m
  • 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)

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

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

Suite, 2 Bedrooms (Duet Suite)

Suite, 2 Bedrooms (Duet Suite)

  • 65 sq m
  • 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)

Suite, 1 King Bed (Hargadine)

  • 84 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

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

Suite, 1 King Bed (Barbara Howard)

Suite, 1 King Bed (Barbara Howard)

  • 46 sq m
  • Sleeps 2
  • 1 King Bed

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

Suite, 1 King Bed (Eleanor Rose)

Suite, 1 King Bed (Eleanor Rose)

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

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

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

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

Suite, 1 Queen Bed with Sofa bed (Brighton)

Suite, 1 Queen Bed with Sofa bed (Brighton)

  • 42 sq m
  • 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)

Suite, 1 Queen Bed with Sofa bed (Courtyard)

  • 42 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

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

Suite, 1 King Bed (Fordyce)

Suite, 1 King Bed (Fordyce)

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

Similar properties

Lobby
Ashland Springs Hotel
  • Spa
  • Pet-friendly
  • Parking included
  • Free Wi-Fi
4.6 out of 5, Wonderful, 1,004 reviews
The price is AU$174
includes taxes & fees
31 Mar - 1 Apr
Ashland Springs Hotel

About the area

Ashland

A stay at Winchester Inn places you in the heart of Ashland, steps from Oregon Cabaret Theatre and 3 minutes by foot from Ashland Library. .This inn is 0.2 mi (0.3 km) from Lithia Park and 0.2 mi (0.3 km) from Oregon Shakespeare Festival.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 1 min walk - 0.0 km
  • Thomas Theatre - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Oregon Shakespeare Festival - 3 min walk - 0.3 km

Getting around

  • Rogue Valley Intl. Airport (MFR) - 22 min drive

Restaurants

  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Skout Taphouse & Provisions - ‬6 min walk
  • ‪Case Coffee Roasters - ‬6 min walk
  • ‪Zoey's Cafe - ‬3 min walk
  • ‪Taqueria Picaro - ‬4 min walk

About this property

Winchester Inn

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.

Make yourself at home in one of the 21 individually decorated guestrooms, featuring minibars and flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.
Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional amenities at this Victorian inn include concierge services and gift shops/newsstands.
At Winchester Inn, enjoy a satisfying meal at the restaurant. Quench your thirst with your favorite drink at the bar/lounge. A complimentary cooked-to-order breakfast is served daily from 8 AM to 9:30 AM.
Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Free self parking is available onsite.
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 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

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

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
  • 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

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
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. 232 out of 270 reviews
Rating 8 - Good. 28 out of 270 reviews
Rating 6 - Okay. 4 out of 270 reviews
Rating 4 - Poor. 3 out of 270 reviews
Rating 2 - Terrible. 3 out of 270 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.6/10

Property conditions & facilities

Reviews

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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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 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

10/10 Excellent

Raul

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

10/10 Excellent

Amy

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

10/10 Excellent

Kathleen

Business traveller
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