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Winchester Inn

3.5 star property
Victorian inn in Historic Downtown District with restaurant and bar/lounge

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your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Winchester Inn

Front of property
Suite, 1 King Bed (Barbara Howard)
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area
Double Room, 1 King Bed (Eastlake)
Suite, 2 Bedrooms (Duet Suite) | Living area

Reviews

9.8 out of 10

Exceptional

Popular amenities

  • Bar
  • Laundry facilities
  • Air conditioning
  • Non-smoking
  • Free parking

Main amenities (12)

  • Daily housekeeping
  • Restaurants 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 price is €126
includes taxes & fees
30 Dec - 31 Dec

Room options

Available filters for rooms
Showing 20 of 20 rooms

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

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio)

Highlights

Furnished 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
Fan
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Bedroom (Garden)

Double Room, 1 Bedroom (Garden)

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 (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Fan
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Single 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)

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 (Eastlake)

Double Room, 1 King Bed (Eastlake)

Double Room, 1 King Bed (Eastlake)

Highlights

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

Double Room, 1 King Bed (Enders)

Double Room, 1 King Bed (Enders)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Fan
  • 37 sq m
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 Bedroom (Sylvan)

Double Room, 1 Bedroom (Sylvan)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Sofa bed
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa 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)

Highlights

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

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 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
  • 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 with Sofa bed (Robert Gordon)

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

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

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 46 sq m
  • 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
  • Sleeps 4
  • 1 King Bed, 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)

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

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

Suite, 1 King Bed (Eleanor Rose)

Suite, 1 King Bed (Eleanor Rose)

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)

Highlights

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

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 42 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

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The price is €150
includes taxes & fees
2 Jan - 3 January 2025
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About the area

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

What's nearby

  • Oregon Cabaret Theatre - 2 min walk
  • Ashland Library - 3 min walk
  • Lithia Park - 4 min walk
  • Oregon Shakespeare Festival - 4 min walk
  • Southern Oregon University - 16 min walk

Getting around

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

Restaurants

  • ‪Brickroom - ‬6 min walk
  • ‪Skout Taphouse & Provisions - ‬6 min walk
  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Greenleaf Restaurant - ‬7 min walk
  • ‪Case Coffee Roasters - ‬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 visit 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 travellers love the helpful staff.

Languages

English

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
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 cots (infant beds)
DONE

Pets

    • Pets not allowed
WIFI

Internet

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

Parking

    • Free on-site 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 reception
  • 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
  • Dressing gowns
  • Iron/ironing board

Sleep well

  • Hypo-allergenic bedding
  • Down duvet
  • Premium bedding
  • Pillow-top mattress

What to enjoy

  • Individually furnished and decorated

Freshen up

  • Designer toiletries
  • Hairdryer
  • 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 checkout. Fees may include applicable taxes:
  • City/local tax: USD 9.0
  • 3 per cent tourism fee will be charged
  • Administrative fee: USD 6.00 per accommodation, per night

Optional extras

  • Late checkout can be arranged for an extra charge

Policies

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
Only registered guests are allowed in the guestrooms.
This property does not have lifts.
This property accepts credit cards. Cash is not accepted.

Also known as

Winchester Inn Ashland
Winchester Inn
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 on-site 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.

Winchester Inn Reviews

Reviews

9.8

Exceptional

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.6/10

Eco-friendliness

Reviews

8/10 Very good

Janet, 1-night trip
Verified Hotels.com guest review

10/10 Exceptional

Beautiful
Gregory, 2-night trip
Verified Orbitz guest review

6/10 Good

The heating/cooling are awful. Some maintenance needs to be done. Takes forever to get hot water. Sink drains are slow. The breakfasts are fantastic! Still, we won't be going back.
Robert, 5-night romance trip
Verified Expedia guest review

10/10 Exceptional

Always a great stop on our travels north and south. Great location. Great restaurant. Rooms are great. Staff are very accommodating, highly recommend
Larry, 1-night trip
Verified Expedia guest review

10/10 Exceptional

Leonilda, 1-night trip
Verified Hotels.com guest review

10/10 Exceptional

Loved the luxurious bedding and sweet delivered to the room daily
Linda, 2-night romance trip
Verified Expedia guest review

10/10 Exceptional

Beautiful, extremely well maintained property in the heart of Ashland with lots of character and deluxe amenities. Very friendly and helpful staff. Gourmet restaurant on premises and superb breakfast with many options. Walk to everything. Highly recommend.
Gregory, 1-night trip
Verified Expedia guest review

10/10 Exceptional

Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend.
Christine, 3-night romance trip
Verified Expedia guest review

10/10 Exceptional

Perfection
Room very nice. Great location. Delicious food.
Kathryn, 2-night trip
Verified Hotels.com guest review

10/10 Exceptional

james, 1-night trip
Verified Hotels.com guest review

10/10 Exceptional

Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants!
Larry, 1-night romance trip
Verified Expedia guest review

10/10 Exceptional

Gregg, 1-night trip
Verified Hotels.com guest review

10/10 Exceptional

Absolutely wonderful property and outstanding service.
Kevin, 1-night romance trip
Verified Orbitz guest review

10/10 Exceptional

The staff was courteous, helpful, and conversational. Rooms were clean and stylish.
Jody, 2-night romance trip
Verified Expedia guest review

8/10 Very good

The food is amazing! Unfortunately, there are many things that should be fixed or upgraded. For the price, it should be in perfect condition.
Robert, 3-night romance trip
Verified Expedia guest review

10/10 Exceptional

Staying at the Winchester Inn is simply stellar beyond compare and it's very convenient to Ashland and walking to the plays.
Donna, 3-night trip
Verified Hotels.com guest review

10/10 Exceptional

cozy is alive and well in ashland
it was cozy and perfect
Robert, 1-night trip
Verified Hotels.com guest review

10/10 Exceptional

The Winchester is idealic. Its so quaint and pretty. They thought of every detail down to a personal greeting in the room and reservations for their complimentary breakfast, which was like eating at a high end restaurant, and the bed is made by the time you return. The room was so clean, and the towels and bedding were really high quality. And the staff were fantastic! I really look forward to staying here again
Starlyn, 2-night trip
Verified Expedia guest review

10/10 Exceptional

Linda, 1-night trip
Verified Hotels.com guest review

6/10 Good

Robert, 1-night trip
Verified Expedia guest review

10/10 Exceptional

Derek, 4-night family trip
Verified Hotels.com guest review

10/10 Exceptional

This was a lovely stopover in Ashland on our way to Santa Barbara. It is a charming, well run inn. This was Memorial Day weekend so breakfast was not “full service” but what we had was delicious.
Kathryn, 1-night trip
Verified Expedia guest review

4/10 Fair

I booked the Garden Room for a Queen bed and a sofa bed. I even asked again when I was shown the room if the sofa made into a bed and ahead of time asked to be sure there would be extra bedding for the sofa bed. I was assured upon check in that the sofa made into a bed. It does not. The Queen is more of a double than a Queen and the other guest had to sleep in the bay window minus extra bedding. I tried to get help by calling front desk, no answer. The dishwasher offered his condolences, the staff are nice, but this is poor service to not be able to reach anyone for help in the evening. Very disappointed.
Karen, 1-night business trip
Verified Expedia guest review

10/10 Exceptional

The service was delightful
Bonnie J, 1-night romance trip
Verified Expedia guest review

8/10 Very good

A good place to stay. They need to work on some maintenance issues, though. The included breakfasts are magnificent!
Robert, 6-night romance trip
Verified Expedia guest review