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Winchester Inn

3.5 star property
Victorian inn in Ashland with restaurant and bar/lounge

Choose dates to view prices

Photo gallery for Winchester Inn

Front of property - Winchester Inn (Ashland)
Suite, 2 Bedrooms (Duet Suite) | Living area | Flat-screen TV - Winchester Inn (Ashland)
Suite, 1 King Bed (Hargadine) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds - Winchester Inn (Ashland)
Bar (on property) - Winchester Inn (Ashland)
Suite, 1 King Bed (Hargadine) | Living room | Flat-screen TV - Winchester Inn (Ashland)
In the heart of Historic Downtown District, Winchester Inn invites you to unwind in its charming garden or on the sun-kissed terrace. Enjoy a cooked-to-order breakfast, connect with WiFi, and take advantage of dry cleaning/laundry services. With a bar for evening relaxation and helpful staff that have left lasting impressions on previous guests.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Bar
  • Laundry facilities
  • Non-smoking
  • 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)

  • Television
  • Garden
  • Terrace
  • Daily housekeeping
  • Coffee/tea maker
  • Minibar
The current price is CNY1,262
CNY1,492 total
includes taxes & fees
Jan 11 - Jan 12, 2026

Room options

Available filters for rooms
Showing 20 of 20 rooms

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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Premium bedding
  • 33 sq m
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
  • 33 sq m
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 33 sq m
  • 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)

Highlights

Balcony or patio
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Marjorie Roy)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Catharine M)

10.0 out of 10
Exceptional
(5 reviews)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 28 sq m
  • 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)

Highlights

Furnished balcony
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Andrew G)

10.0 out of 10
Exceptional
(3 reviews)

Highlights

Furnished balcony
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Peter Benjamin)

Highlights

Furnished patio
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 37 sq m
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 33 sq m
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 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) | 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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 2 Bedrooms (Duet Suite)

Highlights

Furnished patio
Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 65 sq m
  • 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)

Highlights

Furnished balcony
Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Barbara Howard)

Highlights

Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 46 sq m
  • 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)

Highlights

Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 46 sq m
  • 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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 42 sq m
  • 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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 Queen Bed with Sofa bed (Courtyard)

Highlights

Furnished patio
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Fordyce)

10.0 out of 10
Exceptional
(1 review)

Highlights

Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 42 sq m
  • Sleeps 2
  • 1 King 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 - 0.0 km
  • Thomas Theatre - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 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
  • ‪Ruby's - ‬6 min walk
  • ‪The Growler Guys - ‬3 min walk
  • ‪Zoey's Cafe - ‬3 min walk
  • ‪Taqueria Picaro - ‬4 min walk

About this property

Winchester Inn

Enjoy your visit to Ashland with a stay at Winchester Inn. 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

DONE

Hotel size

    • 21 rooms
    • Arranged over 3 floors
DONE

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
DONE

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
DONE

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
DONE

Children

    • No cribs (infant beds)
DONE

Pets

    • Pets not allowed
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms
LOCAL_PARKING

Parking

    • Free onsite self parking
DONE

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

Room amenities

Be entertained

  • Flat-screen television
  • Cable TV channels

Home comfort

  • Air conditioning and heating
  • Fan
  • 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

Stay connected

  • Free WiFi
  • Phone

More

  • Daily housekeeping

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 9.0
  • 3 percent destination fee will be charged
  • Administrative fee: USD 6.00 per accommodation, per night

Optional extras

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

Policies

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

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 4-minute walk from Lithia Park and 4 minutes' walk from Oregon Shakespeare Festival.

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