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Winchester Inn

3.5 star property
Victorian inn with free breakfast and restaurant

Choose dates to view prices

Photo gallery for Winchester Inn

Bar (on property)
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area
Suite, 1 Bedroom (Silverdale) | Living area
Suite, 1 King Bed (Barbara Howard)
Front of property
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

9.8 out of 10
Exceptional

Popular amenities

  • Bar
  • Housekeeping
  • Laundry
  • Air conditioning
  • Free WiFi
The current price is AU$452
includes taxes & fees
15 Sept - 16 Sept

Room options

Check availability for these dates

Tonight

Sept 7 - Sept 8
Check availability for tonight Sept 7 - Sept 8

Tomorrow

Sept 8 - Sept 9
Check availability for tomorrow Sept 8 - Sept 9
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)

9.4 out of 10
Exceptional
(3 reviews)

Highlights

Balcony or 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
Premium bedding
  • 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)

10.0 out of 10
Exceptional
(1 review)

Highlights

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

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

10.0 out of 10
Exceptional
(1 review)

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 and 1 Twin 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)

10.0 out of 10
Exceptional
(3 reviews)

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)

10.0 out of 10
Exceptional
(1 review)

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 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)

10.0 out of 10
Exceptional
(1 review)

Highlights

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

9.6 out of 10
Exceptional
(5 reviews)

Highlights

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

10.0 out of 10
Exceptional
(5 reviews)

Highlights

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

10.0 out of 10
Exceptional
(2 reviews)

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
  • 1 bedroom
  • 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)

7.0 out of 10
Good
(2 reviews)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 46 sq m
  • 1 bedroom
  • 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
  • 2 bedrooms
  • 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)

10.0 out of 10
Exceptional
(1 review)

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)

9.0 out of 10
Wonderful
(2 reviews)

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)

8.0 out of 10
Very good
(1 review)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Twin 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
  • 1 bedroom
  • Sleeps 2
  • 1 Queen 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 guideOpens in a new window
View more Inns in AshlandOpens in a new window
Map
35 S. 2nd St., Ashland, OR, 97520

What's nearby

  • Oregon Cabaret Theatre - 1 min walk - 0.0 km
  • Allen Elizabethan Theatre - 3 min walk - 0.3 km
  • Oregon Shakespeare Festival - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Southern Oregon University - 17 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Skout Taphouse & Provisions - ‬6 min walk
  • ‪Ruby's - ‬6 min walk
  • ‪RedZone Sports Bar N' Grill - ‬1 min walk
  • ‪Brickroom - ‬6 min walk
  • ‪Case Coffee Roasters - ‬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, a gift shop and concierge services
  • Free newspapers, luggage storage and tour/ticket information
  • Guest reviews speak highly of the helpful staff
Room features
All rooms are individually furnished, and include comforts such as premium bedding and air conditioning, in addition to thoughtful touches such as free WiFi and bathrobes.
More conveniences in all rooms include:
  • Heating and fans
  • Hypo-allergenic bedding, Egyptian cotton sheets and pillowtop mattresses
  • Designer toiletries and hairdryers
  • Flat-screen TVs with cable channels
  • Wardrobes/cupboards, electric kettles and daily housekeeping

Property amenities

Internet

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

Parking and transport

  • Free self parking on site

Food and drink

  • Free cooked-to-order breakfast available daily 8 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

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift
  • Wheelchair accessible (may have limitations)

More

  • 3 floors
  • 5 buildings
  • Built in 1886
  • Smoke-free property
  • Victorian architecture

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Dressing gowns
  • Hair dryer
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Fan
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • 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

Access methods

Front desk (limited hours)

Pets

Pets not allowed

Children and extra beds

Children are welcome
Cots (infant beds) are not available

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 9.0
  • 3 per cent destination fee will be charged.
  • Administrative fee: USD 6.00 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

We should mention

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

Property is also known as

Winchester Inn Ashland
Winchester Ashland
The Winchester Inn
Winchester Inn Inn
Winchester Inn Ashland
Winchester Inn Inn Ashland

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 7 Sept 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on 15 Sept 2025 start from AU$429.76, 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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Winchester Inn Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 216 out of 251 reviews
Rating 8 - Good. 27 out of 251 reviews
Rating 6 - Okay. 3 out of 251 reviews
Rating 4 - Poor. 3 out of 251 reviews
Rating 2 - Terrible. 2 out of 251 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.4/10

Eco-friendliness

Reviews

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

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

10/10 Excellent

Amy

Liked: Amenities, property conditions & facilities
Loved our stay so much!
Stayed 2 nights in Feb 2025

10/10 Excellent

Bette

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

10/10 Excellent

Verified traveller

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

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

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

10/10 Excellent

Leonilda

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

Friendly, comfortable & unique place to enjoy

Great beautiful Inn with unique rooms. Delicious breakfast nenu with gluten-free items that are wonderful and I so enjoy
Stayed 1 night in Jan 2025

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

10/10 Excellent

Anita

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place to stay
Stayed 1 night in Nov 2023

10/10 Excellent

Heather

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful location, friendly staff, amazing stay!
Stayed 1 night in May 2023

10/10 Excellent

Chris

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Always a beautiful place to stay!
Stayed 1 night in Oct 2022

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

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

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

10/10 Excellent

Kevin

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

10/10 Excellent

Donna

Liked: Property conditions & facilities, room comfort
Staying at the Winchester Inn is simply stellar beyond compare and it's very convenient to Ashland and walking to the plays.
Stayed 3 nights in Jun 2024

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

8/10 Good

Bradley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff and really clean and comfortable rooms.Love the location and quick walk to local cafe’s and restaurants.
Stayed 2 nights in Oct 2022

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved the luxurious bedding and sweet delivered to the room daily
Stayed 2 nights in Aug 2024

10/10 Excellent

Charlotte

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved our stay as always. Breakfast was also delicious.

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

10/10 Excellent

Becki

Lovely stay. A very unique experience.
Stayed 2 nights in Oct 2024

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the restaurant!
Stayed 1 night in Mar 2022

10/10 Excellent

Janet

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
It is always a treat to stay at The Winchester! Without a doubt, it is my favorite place to stay!
Stayed 4 nights in Jun 2022