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Winchester Inn

3.5 star property
3.5-star Victorian inn near Oregon Shakespeare Festival

Choose dates to view prices

Photo gallery for Winchester Inn

Bar (on property)
A bedroom with a bed, dresser, chair, and a television on the wall.
A living room with a sofa, two armchairs, a coffee table, and a kitchen in the background.
A kitchen with a built-in island, pendant lighting, and a view into the dining area.
Front of property

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services

Explore the area

View in a map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Place, Lithia Park
    ‪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)

Double Room, 1 Bedroom (Garden)

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

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
  • Free WiFi

View all photos for Double Room (Queen Anne)

A hotel room with a large bed, two armchairs, a small table, a TV, and a mirror.

Double Room (Queen Anne)

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

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
  • Free WiFi

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

A bedroom with a bed, a desk, a chair, and a television.

Double Room, 1 Queen Bed (Marjorie Roy)

  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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
  • Free WiFi

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

A spacious bedroom with a large bed, bedside lamps, a wooden headboard, and a piano in the corner.

Double Room, 1 King Bed (Sunset)

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

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

A cozy living room with a beige sofa, a patterned armchair, a small table with a lamp, and a window with curtains.

Double Room, 1 King Bed (Andrew G)

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

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

A bedroom with a large bed, a wooden wardrobe, a sofa, and a small table.

Double Room, 1 King Bed (Peter Benjamin)

  • 37 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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

A well-lit room with a large mirror, a wooden cabinet, a floral armchair, a beige sofa, and a bed with a quilted cover.

Double Room, 1 King Bed (Eastlake)

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

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
  • Free WiFi

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
  • Free WiFi

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

A bedroom with a large bed, bedside lamps, a nightstand, a window with curtains, and a ceiling light.

Suite, 2 Bedrooms (Duet Suite)

  • 65 sq m
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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

A bedroom with a bed, dresser, chair, and a television on the wall.

Suite, 1 King Bed (Hargadine)

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

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

A four-poster bed with a canopy, a bedside table with a lamp, a dresser with mirrors, and a view of the outdoors through a window.

Suite, 1 King Bed (Barbara Howard)

  • 46 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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
  • Free WiFi

View all photos for Suite, 1 Bedroom (Silverdale)

A bedroom with a wooden ceiling, a bed with floral bedding, a chair, a desk, and a framed picture on the wall.

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 Twin Murphy Bed
  • Free WiFi

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

A neatly arranged bedroom with a large bed, two bedside tables, a dresser, and a window with curtains.

Suite, 1 Queen Bed with Sofa bed (Brighton)

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

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
  • Free WiFi

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

A bedroom with a large bed, two bedside lamps, a fireplace, and a view of the outdoors.

Suite, 1 King Bed (Fordyce)

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

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 WiFi

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 Twin Bed
  • Free WiFi

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 WiFi

About the area

Ashland

Heart of Ashland.A stay at this Historic Downtown District inn places you steps from Oregon Cabaret Theatre and within a 5-minute walk of Oregon Shakespeare Festival. Ashland Library and Lithia Park are also within half a mile (1 km).
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 1 min walk - 0.1 km
  • Oregon Shakespeare Festival - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 5 min walk - 0.4 km
  • Angus Bowmer Theatre - 5 min walk - 0.4 km

Getting around

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

Restaurants

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

About this property

Winchester Inn

3.5-star Victorian inn near 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.

  • 21 guestrooms or units
  • 3 levels
  • 5 buildings
  • Built in 1886
  • Cooked-to-order breakfast (free)
  • Dry cleaning
  • Front desk (limited hours)
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Terrace
  • Garden
  • Gift shop
  • Newspapers in lobby (free)
  • No smoking on site
  • Bar or lounge
  • 1 conference room
  • Dining venue
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. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Similar properties

Garden
Ashland Springs Hotel
Historic Downtown District
  • Spa
  • Pet friendly
  • Parking included
  • Free WiFi
4.6 out of 5, Wonderful, 1,006 reviews
The price is CA $267
CA $321 total
includes taxes & fees
Jul 26 - Jul 27
Ashland Springs Hotel

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

Accessibility

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

Room amenities

Entertainment

  • Flat-screen TV with cable channels

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

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.
  • Cribs (infant beds) are not available.

Property payment types

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 percent 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

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in each accommodation.

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

Frequently asked questions

How close is Winchester Inn to the airport?

Winchester Inn is 15.7 mi (22-min drive) away from the Rogue Valley Intl. Airport (MFR) airport, the closest popular airport to the property.

How much does it cost to stay at Winchester Inn?

As of Jul 2, 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on Jul 5, 2026 start from CA $307, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does Winchester Inn have an airport shuttle?

Airport shuttle services are not available at Winchester Inn.

Does Winchester Inn offer free breakfast?

Winchester Inn offers free cooked-to-order breakfast every day from 8 AM to 9:30 AM.

Is there a casino at Winchester Inn?

No, there is no casino at this inn, but Ko-Kwel Casino Resort Medford (17-min drive) is nearby.

What time is check-in at Winchester Inn?

Check-in start time: 4:00 PM; Check-in end time: 9 PM.

Is there free parking at Winchester Inn?

This inn offers free self parking.

Does Winchester Inn have a pool?

Winchester Inn does not have a pool.

Does Winchester Inn have a restaurant?

Yes, there is a restaurant on site.

Does Winchester Inn have a spa?

There are no spa services available at this inn.

How close is Winchester Inn to downtown Ashland?

Winchester Inn is 0.2 mi away from Ashland.

Winchester Inn Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 238 out of 276 reviews
Rating 8 - Good. 28 out of 276 reviews
Rating 6 - Okay. 4 out of 276 reviews
Rating 4 - Poor. 3 out of 276 reviews
Rating 2 - Terrible. 3 out of 276 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.6/10

Property conditions & facilities

Reviews