Winchester Inn

Property class: 3.5
Victorian inn in Ashland with restaurant and bar/lounge

Choose dates to view prices

Winchester Inn is a great choice for a stay in Ashland. Guests looking for a bite to eat can check out the restaurant, and the bar/lounge is the perfect spot to grab a drink at the end of the day. Other highlights at this Victorian inn include a terrace and a garden. Fellow travelers love the helpful staff.

Reviews

9.6 out of 10, Loved by guests
Top-rated by travelers

Popular amenities

  • Free parking
  • Free WiFi
  • Connecting rooms available
  • Air conditioning

Main amenities (12)

  • Daily housekeeping
  • Restaurant and bar/lounge
  • Terrace
  • Air conditioning
  • Garden
  • Laundry service
  • Meeting room
  • Concierge services
  • Gift shops/newsstands
  • Free newspapers in the lobby
  • Luggage storage
  • Limited hour front desk

Feel at home (6)

  • Connecting/adjoining rooms available
  • Television
  • Garden
  • Terrace
  • Daily housekeeping
  • Coffee/tea maker
$215 nightly
The total price is $239
Sep 20 - Sep 21
Total with taxes and fees

Room options

Available filters for rooms
Showing 23 of 23 rooms

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

A bedroom with a large bed, a sofa, a small table, and a dresser. There is a window with curtains and a view of greenery outside.

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)

A bedroom with a bed, bedside lamps, a window with curtains, a sofa, a small table, and a bathroom with a sink and mirror.

Double Room, 1 Bedroom (Sylvan)

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

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)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Bed

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

A bedroom with a large bed, a chair, a desk, and a window with curtains.

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)

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

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)

A bedroom with a large bed, a bedside table with a lamp, a wardrobe, and a window with curtains.

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)

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

Double Room, 1 King Bed (Sunset)

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

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)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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)

  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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
(2 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 King Bed

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

A hotel room with a bed, a sofa, a desk with a coffee maker, and a TV on the wall.

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)

A bedroom with a large bed, wooden furniture, and a view of the outdoors.

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

7.0 out of 10
Good
(2 reviews)
  • 500 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Twin Sofa Bed

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)

  • 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)

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

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)

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)

  • 500 sq ft
  • Sleeps 2
  • 1 King Bed

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

A bedroom with a high, sloped ceiling, a large bed, two bedside tables, a chair, and a window.

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)

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)
  • 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)

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)

  • 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)

A bedroom with a bed, bedside table, lamp, and a window with blinds.

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)

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)
  • 450 sq ft
  • Sleeps 2
  • 1 King Bed

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

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
  • 850 sq ft
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Twin Bed

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
  • 500 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

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About the neighborhood

Map
35 S. 2nd St., Ashland, OR, 97520

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
  • ‪Louie's Bar and Grill - ‬6 min walk
  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Case Coffee Roasters - ‬6 min walk
  • ‪Ruby's - ‬6 min walk

About this property

Winchester Inn

  • Winchester Inn is a great choice for a stay in Ashland. Guests looking for a bite to eat can check out the restaurant, and the bar/lounge is the perfect spot to grab a drink at the end of the day. Other highlights at this Victorian inn include a terrace and a garden. Fellow travelers love the helpful staff.

At a glance

Hotel size

    • 21 rooms
    • Arranged over 3 floors

Arriving/Leaving

    • 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 time is 11 AM

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

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21

Children

    • No cribs (infant beds)

Pets

    • Pets not allowed

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms

Parking

    • Free onsite self parking

Other information

    • Smoke-free property

Property amenities

Food and drink

  • Free cooked-to-order breakfast each morning 8 AM–9:30 AM
  • Restaurant
  • Bar/lounge

Working away

  • Meeting room

Services

  • Front desk (limited hours)
  • Concierge services
  • Tour/ticket assistance
  • Dry cleaning/laundry services
  • Free newspapers in lobby
  • Luggage storage

Facilities

  • 5 buildings/towers
  • Built in 1886
  • Garden
  • Terrace
  • Victorian architecture

Accessibility

  • Hardwood flooring in room
  • High pile carpet in room

Room amenities

Be entertained

  • Flat-screen television
  • Cable TV channels

Home comfort

  • Air conditioning and heating
  • Minibar
  • Coffee/tea maker
  • Electric kettle
  • Bathrobes
  • Iron/ironing board

Sleep well

  • Hypo-allergenic bedding
  • Down comforter
  • Premium bedding
  • Pillowtop mattress

What to enjoy

  • Individually furnished and decorated

Freshen up

  • Designer toiletries
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Laptop-friendly workspace
  • Free WiFi
  • Phone

More

  • Daily housekeeping
  • Connecting/adjoining rooms available

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or check-out. Fees may include applicable taxes:
  • A tax is imposed by the city: USD 9
  • Administrative fee: USD 10.00 per accommodation, per night
  • 4 percent destination fee will be charged

Optional extras

  • Late check-out can be arranged for an extra charge

Policies

Extra-person charges may apply and vary depending on property policy.

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.

The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation.

Only registered guests are allowed in the guestrooms.

This property does not have elevators.

Guests can rest easy knowing there's a fire extinguisher on site.

This property accepts credit cards. Cash is not accepted.

Credit cards accepted: Visa, Mastercard, American Express, Discover

Also known as

Winchester Inn Ashland

Winchester Ashland

The Winchester Inn

Winchester Inn Inn

Winchester Inn Ashland

Winchester Inn Inn Ashland

Frequently asked questions

Are pets allowed at Winchester Inn?

Sorry, pets aren't allowed.

Is parking offered on site at Winchester Inn?

Yes, there's free self parking.

What are the check-in and check-out times at Winchester Inn?

Check-in start time: 4:00 PM; Check-in end time: 9 PM. Check-out time is 11 AM. Late check-out is available for a charge.

Is there an onsite casino at Winchester Inn?

No, this inn doesn't have a casino, but Ko-Kwel Casino Resort Medford (17-min drive) is nearby.

What is there to do at Winchester Inn and nearby?

Winchester Inn has a garden.

Are there restaurants at or near Winchester Inn?

Yes, there's an onsite restaurant.

What's the area around Winchester Inn like?

Winchester Inn is in Historic Downtown District, a short 2-minute walk from Oregon Cabaret Theatre and 4 minutes' walk from Lithia Park.

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