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Winchester Inn

3.5 star property
Victorian inn with free breakfast and restaurant

Photo gallery for Winchester Inn

Bar (on property)
Front of property
Suite, 1 King Bed (Barbara Howard)
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area
Suite, 1 Bedroom (Silverdale) | Living area

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Laundry
  • Bar
  • Housekeeping
  • Air conditioning
The current price is NZ$374
includes taxes & fees
27 Oct - 28 Oct

Explore the area

View map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Place, Lithia Park
    ‪3 min walk‬
  • Place, Southern Oregon University
    ‪17 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪25 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
  • 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)

Highlights

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

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
Premium bedding
  • 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)

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)

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
Premium bedding
  • 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)

Highlights

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

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)

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)

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)

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
Premium bedding
  • 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)

Highlights

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

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)

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)

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)

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)

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)

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)

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)

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)

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

About the area

Ashland

Winchester Inn places you in the centre of Ashland, steps from Oregon Cabaret Theatre and within a short 5-minute stroll of Ashland Library. Highlights at this Victorian inn include free cooked-to-order breakfast, a restaurant and free self-parking. .The inn's own lounge bar is a nice place to enjoy a drink. Additionally, you'll find free Wi-Fi in public areas, concierge services and a terrace. Each morning free breakfast is served. .Places within a 5-minute walk of this 3.5-property class Historic Downtown District inn include Lithia Park and Oregon Shakespeare Festival.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 1 min walk - 0.0 km
  • Allen Elizabethan Theatre - 3 min walk - 0.3 km
  • Oregon Shakespeare Festival - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Southern Oregon University - 17 min walk - 1.4 km

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 22 min drive

Restaurants

  • ‪Ruby's - ‬6 min walk
  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪RedZone Sports Bar N' Grill - ‬1 min walk
  • ‪The Growler Guys - ‬3 min walk
  • ‪Blue Toba - ‬4 min walk

About this property

Winchester Inn

Victorian inn with free breakfast and restaurant
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 duvets and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries and hairdryers. Guests can surf the web using complimentary wireless Internet access. Additionally, rooms include an iron/ironing board and fans. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

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Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transport

  • Free self parking on site

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

Access methods

Front desk (limited hours)

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Cots (infant beds) are not available.

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 9.0
  • 3 per cent destination fee will be charged.
  • Administrative fee: USD 6.00 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. 

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.

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

Is parking available at Winchester Inn?

Yep, Winchester Inn has a free self car park.

How much does it cost to stay at Winchester Inn?

As of 2 Oct 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on 27 Oct 2025 start from NZ$353.26, including 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.

What makes Winchester Inn a romantic place to stay?

A lounge bar, plus pillowtop beds in the guestrooms, help set the scene for a romantic weekend at Winchester Inn.

Does Winchester Inn serve breakfast?

Yeah, free cooked-to-order breakfast is available daily between 8 AM and 9:30 AM.

Is there a free airport shuttle available at Winchester Inn?

No, Winchester Inn does not offer an airport shuttle service.

Is there a bar or restaurant at Winchester Inn?

Yep, they've got a lounge bar and an onsite restaurant.

What time are check-in & check-out at Winchester Inn?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Are pets allowed at Winchester Inn?

No, pets are not allowed.