Winchester Inn

Property class: 3.5

Choose dates to view prices

Consider a stay at Winchester Inn and take advantage of free cooked-to-order breakfast, a terrace and a garden. Stay connected with free in-room WiFi, and guests can find other amenities, such as dry cleaning/laundry services and a bar.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free Wi-Fi
  • Air-conditioning
  • Business services
The current price is AU$235
includes taxes & fees
9 Nov - 10 Nov

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

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

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 Single Bed

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

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

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

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)

9.4 out of 10
Exceptional
(3 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed

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

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

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

View all photos for Double Room, 1 King Bed (Enders)

A hotel room with a bed, a sofa, a desk with a coffee maker, and a TV on the wall.

Double Room, 1 King Bed (Enders)

10.0 out of 10
Exceptional
(1 review)
  • 37 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 King Bed with Sofa bed (Robert Gordon)

A bedroom with a large bed, wooden furniture, and a view of the outdoors.

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

7.0 out of 10
Good
(2 reviews)
  • 46 sq m
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Single Sofa Bed

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

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

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

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

A bedroom with a high, sloped ceiling, a large bed, two bedside tables, a chair, and a window.

Suite, 1 King Bed (Eleanor Rose)

9.0 out of 10
Wonderful
(2 reviews)
  • 46 sq m
  • Sleeps 2
  • 1 King Bed

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 Single Murphy Bed

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

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

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
(2 reviews)
  • 42 sq m
  • Sleeps 2
  • 1 King Bed

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

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 Single Bed

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
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About the area

Located in Historic Downtown District, a neighbourhood 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 wood duck standing on rocks with moss and greenery in the background.
    Lithia Park
    3 min walk - 0.3 km
  • Oregon Cabaret Theatre
    1 min walk - 0.1 km
  • Allen Elizabethan Theatre
    5 min walk - 0.4 km
  • Thomas Theatre
    5 min walk - 0.4 km

Getting around

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

Restaurants

  • Skout Taphouse & Provisions
    6 min walk
  • Louie's Bar and Grill
    6 min walk
  • Martolli's Hand Tossed Pizza
    5 min walk
  • Case Coffee Roasters
    6 min walk
  • Ruby's
    6 min walk

About this property

Winchester Inn

  • Inn located in Historic Downtown District
  • 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 such as:
    • Free self-parking
    • Smoke-free property, free newspapers and a gift shop
    • Tour/ticket information, luggage storage and concierge services
    • Guest reviews speak highly of the helpful staff
  • Room features
  • All guest rooms are individually furnished, and include comforts, such as premium bedding and laptop-friendly workspaces, in addition to thoughtful touches, such as air conditioning and bathrobes.
  • More conveniences in all rooms include:
    • Hypo-allergenic bedding, Egyptian cotton sheets and pillowtop mattresses
    • Designer toiletries and hairdryers
    • Flat-screen TVs with cable channels
    • Wardrobes/cupboards, electric kettles and heating

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  • Spa
  • Pet-friendly
  • Parking included
  • Free Wi-Fi
9.2 out of 10, Wonderful, 1,003 reviews
The price is AU$170
includes taxes & fees
1 Dec - 2 Dec
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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 1 Nov 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on 9 Nov 2026 start from AU$235, 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.

How much is parking at Winchester Inn?

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?

Checkout is at 11 AM. Late checkout 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, Ashland Library and Lithia Park. Oregon Shakespeare Festival and Thomas Theatre 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. 250 out of 291 reviews
Rating 8 - Good. 29 out of 291 reviews
Rating 6 - Okay. 6 out of 291 reviews
Rating 4 - Poor. 3 out of 291 reviews
Rating 2 - Terrible. 3 out of 291 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing breakfasts, friendly staff, best location
Stayed 2 nights in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This inn is very sweet - and so well located. The room was spacious enough and the cooked breakfast option was a total highlight. The rooms, I said
Stayed 3 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The property is very charming, and comfortable with beautiful gardens and outdoor spaces. The breakfast choices were delicious and dinner was also exceptional. Staff is very warm, friendly and helpful. I recommend highly.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a wonderful time at the Winchester Inn! It’s an absolutely charming inn with a great location. Rooms and staff and breakfast were all fabulous. We will be back!
Stayed 1 night in Aug 2026
Verified review

6/10 Okay

Liked: Staff & service
The property, location, and staff were amazing!!! However, the room itself was a little underwhelming due to hearing the upstairs guests all night, the bedroom window opening up to the trash bins, and the shower being extremely cold. Additionally someone woke me up at 3 am drumming on the trash bins, it made me feel unsafe.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

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

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

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

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

10/10 Excellent

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

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

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

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

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

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

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

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

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

10/10 Excellent

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

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

10/10 Excellent

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

8/10 Good

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

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

10/10 Excellent

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

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