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Winchester Inn

3.5 star property
Downtown Winchester Inn combines historic charm with warm hospitality, offering a peaceful garden retreat and freshly made breakfast before guests explore the area

Choose dates to view prices

Located in the Historic Downtown District, Winchester Inn welcomes travelers with a charming garden and sunny terrace. Enjoy a cooked-to-order breakfast, WiFi, and convenient dry cleaning services. The helpful staff and bar provide perfect spots for relaxation.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
The current price is ₩258,644
₩314,325 total
includes taxes & fees
Aug 10 - Aug 11

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)
  • 33 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Bed
  • Free WiFi

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)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)
  • 28 sq m
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

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)

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

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)

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

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)
  • 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)

A bedroom with a large bed, bedside lamps, a nightstand, a window with curtains, and a ceiling light.

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)

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

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)

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)

  • 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)

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)
  • 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)

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)

  • 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)

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

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)

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

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
  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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
  • 79 sq m
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Twin Bed
  • Free WiFi

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
  • 46 sq m
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi
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About the neighborhood

Located in Historic Downtown District, a neighborhood in Ashland, Winchester Inn is in a shopping district. Weisinger Family Winery and Grizzly Peak Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore North Mountain Park and Cascade-Siskiyou National Monument. ScienceWorks Hands-On Museum and The RRRink are also worth visiting. Visit our Ashland travel guide
View more Inns in Ashland
Map
35 S. 2nd St., Ashland, OR, 97520

What's nearby

  • A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.
    Oregon Shakespeare Festival
    3 min walk - 0.3 km
  • A pond with ducks, surrounded by trees and a small bridge.
    Lithia Park
    3 min walk - 0.3 km
  • Oregon Cabaret Theatre
    1 min walk - 0.1 km
  • Thomas Theatre
    5 min walk - 0.4 km
  • Allen Elizabethan Theatre
    5 min walk - 0.4 km

Getting around

  • Rogue Valley Intl. Airport (MFR)
    22 min drive

Restaurants

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

About this property

Winchester Inn

  • Inn near Oregon Shakespeare Festival
  • You can look forward to free cooked-to-order breakfast, a terrace, and a garden at Winchester Inn. Free in-room WiFi is available to all guests, along with dry cleaning/laundry services and a bar.
  • You'll also find perks like:
    • Free self parking
    • Smoke-free premises, a gift shop, and concierge services
    • Free newspapers, luggage storage, and tour/ticket assistance
    • Guest reviews give top marks for the helpful staff
  • Room features
  • All guestrooms are individually furnished, and feature comforts such as premium bedding and laptop-friendly workspaces, in addition to thoughtful touches like air conditioning and bathrobes.
  • Extra conveniences in all rooms include:
    • Hypo-allergenic bedding, Egyptian cotton sheets, and pillowtop mattresses
    • Designer toiletries and hair dryers
    • Flat-screen TVs with cable channels
    • Wardrobes/closets, electric kettles, and heating

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The price is ₩198,456
₩235,677 total
includes taxes & fees
Aug 30 - Aug 31
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Property amenities

Internet

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

Parking and transportation

  • Free self parking on site

Food and drink

  • Free cooked-to-order breakfast available daily 8:00 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

  • Hardwood flooring in room
  • High-pile carpet in room
  • No elevator

More

  • 3 floors
  • 5 buildings
  • Built in 1886
  • Smoking not allowed
  • Victorian architecture

Room amenities

Bedroom

  • Down comforter
  • Egyptian cotton sheets
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Connecting rooms available
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop workspace
  • 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
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

Pets not allowed

Children and extra beds

Children are welcome
Cribs (infant beds) are not available

Property payment types

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • A tax is imposed by the city: USD 9
  • 4 percent destination fee will be charged
  • Administrative fee: USD 10.00 per accommodation, per night

We have included all charges provided to us by the property.

Optional extras

  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

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
Safety features at this property include a fire extinguisher
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

We should mention

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

Frequently asked questions

Is Winchester Inn pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Winchester Inn?

As of Aug 3, 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on Aug 10, 2026 start from ₩258,644, excluding 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.

How much is parking?

Self parking is free at this property.

What time is check-in at Winchester Inn?

Check-in start time: 4:00 PM; Check-in end time: 9 PM. Late check-in is available during limited hours.

What time is check-out at Winchester Inn?

Check-out is at 11 AM. Late check-out is available for a fee.

Where is Winchester Inn located?

Located in Historic Downtown District, this inn is within a 5-minute walk of Oregon Cabaret Theatre and Oregon Shakespeare Festival. Ashland Library and Lithia Park are also within 5 minutes.

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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
Rating 10 - Excellent. 244 out of 282 reviews
Rating 8 - Good. 28 out of 282 reviews
Rating 6 - Okay. 4 out of 282 reviews
Rating 4 - Poor. 3 out of 282 reviews
Rating 2 - Terrible. 3 out of 282 reviews

Reviews

Verified review

10/10 Excellent

Sara

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our stay, as always, was wonderful! Our room was comfortable and clean, and we love the afternoon treats delivered to our room. The staff is always helpful and friendly, and you can’t beat the daily breakfasts. We also enjoy at least one delicious dinner at Alchemy, which always impresses. It’s an easy walk to shows during OSF and downtown shops and restaurants. We look forward to our return.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!
Stayed 1 night in Sep 2025
Verified review

10/10 Excellent

Stacey

Liked: Cleanliness, amenities, property conditions & facilities
The room is fantastic!! Highly recommend!
Stayed 1 night in Jan 2026
Verified review

10/10 Excellent

Dirk

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, really comfortable bed, pillows and sheets!
Stayed 1 night in Jun 2025
Verified review

10/10 Excellent

Carolyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful room with comfortable bed. Nice quality bedding.
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Paula

Liked: Cleanliness, staff & service, property conditions & facilities
This is such a fantastic place to stay in Ashland Oregon. The accommodations are lovely and the on-site restaurant is truly incredible.
Stayed 2 nights in Sep 2023
Verified review

10/10 Excellent

Christi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a unique Victorian place! So charming, clean and spacious….
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Awesome location and amazing included breakfast. The bed was cozy and Eastlake room was delightful.
Stayed 2 nights in Oct 2024
Verified review

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Lovely room
Stayed 1 night in Oct 2025
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable.
Stayed 2 nights in Apr 2025
Verified review

10/10 Excellent

Kevin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely wonderful property and outstanding service.
Stayed 1 night in Jun 2024
Verified review

10/10 Excellent

Kathleen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!!
Stayed 1 night in Feb 2025
Verified review

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
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.
Stayed 1 night in Jul 2025
Verified review

10/10 Excellent

Baki

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Oct 2024
Verified review

10/10 Excellent

Larry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always a great stop on our travels north and south. Great location. Great restaurant. Rooms are great. Staff are very accommodating, highly recommend
Stayed 1 night in Aug 2024
Verified review

10/10 Excellent

william

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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.
Stayed 1 night in Sep 2023
Verified review

8/10 Good

Robert

Liked: Cleanliness, staff & service, amenities
A good place to stay. They need to work on some maintenance issues, though. The included breakfasts are magnificent!
Stayed 6 nights in Apr 2024
Verified review

10/10 Excellent

Rob

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 1 night in Nov 2024
Verified review

10/10 Excellent

Christine

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend.
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Bonnie J

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The service was delightful
Stayed 1 night in May 2024
Verified review

10/10 Excellent

Len

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Jody

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The staff was courteous, helpful, and conversational. Rooms were clean and stylish.
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

Larry

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants!
Stayed 1 night in Jul 2024
Verified review

10/10 Excellent

Diana

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

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.
Stayed 2 nights in Jan 2025
Verified review

10/10 Excellent

Shanna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 2 nights in Sep 2025