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Winchester Inn

3.5 star property
Victorian inn with restaurant, near Oregon Shakespeare Festival

Choose dates to view prices

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, Loved by guests
Top-rated by travelers

Popular amenities

  • Free parking
  • Free WiFi
  • Air conditioning
  • Bar

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 CNY1,899
CNY2,270 total
includes taxes & fees
May 31 - Jun 1

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)
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

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)
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

Double Room, 1 Queen Bed (Marjorie Roy) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

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

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

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)

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

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)
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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) | 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)
  • 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)

Suite, 2 Bedrooms (Duet Suite) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

Suite, 1 King Bed (Hargadine) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

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)
  • 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)

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)

  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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)

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)
  • 42 sq m
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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9.2 out of 10, Wonderful, 1,008 reviews
The price is CNY888
CNY1,097 total
includes taxes & fees
May 31 - Jun 1
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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

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

About this property

Winchester Inn

  • Winchester Inn offers a fantastic location, putting you just a 5-minute walk from Oregon Shakespeare Festival. 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
  • 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

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

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Reviews

Winchester Inn Reviews

9.6

Exceptional

9.8

Cleanliness

9.6

Location

9.8

Staff & service

9.6

Property conditions & facilities

Guest review summary

What guests liked

  • Breakfast options were fantastic, with many choices and high-end quality. (26 reviews)
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From real guest reviews summarized by AI.

Popular mentions

Service staff
Room
Breakfast
Restaurant
Food
Location
Bed
Bathroom
Downtown
Walking

Reviews

Verified

10/10 Exceptional

The room is fantastic!! Highly recommend!
Stacey, 1-night trip
Verified

10/10 Exceptional

Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!
Laura, 1-night trip
Verified

10/10 Exceptional

Beautiful room with comfortable bed. Nice quality bedding.
Carolyn, 1-night trip
Verified

10/10 Exceptional

Beautiful property, really comfortable bed, pillows and sheets!
Dirk, 1-night trip
Verified

10/10 Exceptional

Such a unique Victorian place! So charming, clean and spacious….
Christi, 2-night trip
Verified

10/10 Exceptional

Lovely room
Patricia, 1-night trip
Verified

10/10 Exceptional

This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.
Paula, 2-night trip
Verified

10/10 Exceptional

Awesome location and amazing included breakfast. The bed was cozy and Eastlake room was delightful.
Jennifer, 2-night trip
Verified

10/10 Exceptional

Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable.
2-night trip
Verified

10/10 Exceptional

This inn offers a relaxing and comfortable stay. The location is centrally located in the heart of Ashland and the accomodations are amazing. We loved the welcome cookies and the breakfast was incredible. The Victorian architecture of the Inn, the gardens, and surrounding cottages were beatiful. There were so many places to sit and enjoy the gardens, food, and drinks.
Nick, 1-night trip
Verified

10/10 Exceptional

Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!!
Kathleen, 1-night trip
Verified

10/10 Exceptional

Absolutely wonderful property and outstanding service.
Kevin, 1-night trip
Verified

10/10 Exceptional

Booked this last minute and was very pleased-very friendly staff, great clean room, very close to restaurants, and a wonderful complimentary real breakfast! I would definitely choose this place again.
Baki, 1-night trip
Verified

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

10/10 Exceptional

quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention.
Len, 2-night trip
Verified

10/10 Exceptional

Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.
Shanna, 2-night trip
Verified

10/10 Exceptional

Great hotel

This is an excellent hotel. Large room, immaculate furnishings (room cookies too!) and excellent breakfast, plus it is perfectly located to stroll Ashland. Highly recommended.
william, 1-night trip
Verified

10/10 Exceptional

Winchester Inn is great place to stay in Ashland. The rooms are spacious, well furnished, clean, and comfy. It is close to the theaters and downtown area so you don't have to drive anywhere once you check in. There are a number of breakfast options and the food is excellent. We would definitely stay there again!
Rob, 1-night trip
Verified

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 trip
Verified

10/10 Exceptional

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

10/10 Exceptional

The service was delightful
Bonnie J, 1-night trip
Verified

10/10 Exceptional

Beautiful setting with great service and food. Only problem was the bees nest above our patio room. Couldn’t sit outside because of the bees.
Bette, 2-night trip
Verified

10/10 Exceptional

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

8/10 Very good

The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.
Sid, 2-night trip
Verified

10/10 Exceptional

Wonderful

The Winchester, especially the Hargadine Suite, is the best hotel on the west coast. I love it so much it is a very very uniquely special place. I go to Ashland specifically for the Winchester and their amazing breakfast.
Diana, 2-night trip