Winchester Inn

Property class: 3.5
Inn near Lithia Park

Choose dates to view prices

Historic Downtown District is home to Winchester Inn, a 3.5-star inn centrally located in Ashland. Guests can enjoy the Victorian-style charm while relaxing on the terrace or unwinding in the separate living room. The inn features a restaurant and a bar & lounge for convenient dining options. Free Wi-Fi, free parking, and free breakfast enhance the value of the stay. Travelers loved the awesome location, cozy beds, and great rooms at the hotel. Nearby attractions include Lithia Park and Ashland Library.

Reviews

9.6 out of 10, Loved by guests
Top-rated by travelers

Popular amenities

  • Free parking
  • Free WiFi
  • Connecting rooms available
  • Air conditioning
$155 nightly
The total price is $173
Nov 5 - Nov 6
Total with taxes and fees

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)
  • 350 sq ft
  • 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)
  • 350 sq ft
  • 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)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Twin 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)
  • 350 sq ft
  • 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)

  • 350 sq ft
  • 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)
  • 300 sq ft
  • 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)
  • 400 sq ft
  • 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)
  • 400 sq ft
  • 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)

  • 400 sq ft
  • 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)
  • 350 sq ft
  • 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)
  • 400 sq ft
  • 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)
  • 500 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Twin 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)

  • 700 sq ft
  • 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)

  • 900 sq ft
  • 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)

  • 500 sq ft
  • 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)
  • 500 sq ft
  • 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)
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Twin 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)

  • 450 sq ft
  • 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)

  • 450 sq ft
  • 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)
  • 450 sq ft
  • 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
  • 450 sq ft
  • 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
  • 850 sq ft
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Twin 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
  • 500 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed

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9.2 out of 10, Wonderful, 1,005 reviews
$108 nightly
The price is $120
Dec 1 - Dec 2
Total with taxes and fees
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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
  • Thomas Theatre - 5 min walk - 0.4 km

Getting around

  • Rogue Valley Intl. Airport (MFR) - 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

  • Winchester Inn is a great choice for a stay in Ashland. 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

Hotel size

    • 21 rooms
    • Arranged over 3 floors

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

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

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

Children

    • No cribs (infant beds)

Pets

    • Pets not allowed

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms

Parking

    • Free onsite self parking

Other information

    • Smoke-free property

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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 was consistently described as delicious, heavenly, and a highlight of the stay. (32 reviews)
  • The on-site restaurant offers excellent food, great service, and a variety of options for breakfast and dinner. (26 reviews)
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From real guest reviews summarized by AI.
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Popular mentions

Service staff
Room
Breakfast
Restaurant
Food
Bed
Location
Bathroom
Store
Downtown

Reviews

Verified review

10/10 Exceptional

Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely stay there again.
Verified review

10/10 Exceptional

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!
Verified review

10/10 Exceptional

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.
Verified review

10/10 Exceptional

Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!
Verified review

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.
Verified review

10/10 Exceptional

The room is fantastic!! Highly recommend!
Verified review

10/10 Exceptional

Beautiful property, really comfortable bed, pillows and sheets!
Verified review

10/10 Exceptional

Awesome location and amazing included breakfast. The bed was cozy and Eastlake room was delightful.
Verified review

10/10 Exceptional

Beautiful room with comfortable bed. Nice quality bedding.
Verified review

10/10 Exceptional

Absolutely wonderful property and outstanding service.
Verified review

10/10 Exceptional

Such a unique Victorian place! So charming, clean and spacious….
Verified review

10/10 Exceptional

Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable.
Verified review

10/10 Exceptional

Comfortable rooms with many amenities. Their sister restaurant across the street, Chateaubriand, is amazing!!!
Verified review

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.
Verified review

10/10 Exceptional

Lovely room
Verified review

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.
Verified review

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.
Verified 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
Verified review

8/10 Very good

A good place to stay. They need to work on some maintenance issues, though. The included breakfasts are magnificent!
Verified review

10/10 Exceptional

The service was delightful
Verified review

10/10 Exceptional

Incredibly friendly and helpful staff. Gorgeous accommodations and oh so quiet and peaceful. Amazing breakfast! Highly recommend.
Verified review

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!
Verified review

10/10 Exceptional

The staff was courteous, helpful, and conversational. Rooms were clean and stylish.
Verified review

10/10 Exceptional

Staff was excellent! Room is beautiful! Well stocked! Easy access to restaurants!
Verified review

10/10 Exceptional

quaint room. Fantastic restaurant. Excellent staff. Grounds need some sttention.