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Winchester Inn

3.5 star property
Victorian inn in Ashland with restaurant and bar/lounge

Choose dates to view prices

Photo gallery for Winchester Inn

Enjoy a drink at the bar, surrounded by lush views and comfortable seating.
Enjoy cooking in this well-equipped kitchen with a dishwasher and sink.
Relax in a classic, elegantly decorated room with a four-poster bed and comfortable seating area.
Relax in this inviting living area with a sofa, chair, and table, offering a peaceful escape.
Traditional Victorian-style house with a wrap-around balcony and well-maintained garden.
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
Exceptional

Popular amenities

  • Laundry facilities
  • Bar
  • Air conditioning
  • Non-smoking

Main amenities (12)

  • Daily housekeeping
  • Restaurants 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 S$350
includes taxes & fees
4 Aug - 5 Aug

Room options

Check availability for these dates

Tonight

Jul 30 - Jul 31
Check availability for tonight Jul 30 - Jul 31

Tomorrow

Jul 31 - Aug 1
Check availability for tomorrow Jul 31 - Aug 1
Available filters for rooms
Showing 20 of 20 rooms

View all photos for Double Room, 1 Queen Bed (Patio)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

Double Room, 1 Queen Bed (Patio)

10.0 out of 10
Exceptional
(2 reviews)

Highlights

Furnished 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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Egyptian cotton bed sheets
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Double Room, 1 Bedroom (Garden)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Fan
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Double Room (Queen Anne)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Egyptian cotton bed sheets
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Single Bed

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

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Egyptian cotton bed sheets
  • 33 sq m
  • Sleeps 2
  • 1 King Bed

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

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Egyptian cotton bed sheets
  • 37 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Double Room, 1 Bedroom (Sylvan)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Down duvet
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Double Room, 1 Queen Bed (Catharine M)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
Egyptian cotton bed sheets
  • 28 sq m
  • Sleeps 2
  • 1 Queen Bed

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

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 King Bed (Barbara Howard)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
  • Sleeps 2
  • 1 King Bed and 1 Double Sofa Bed

View all photos for Suite, 2 Bedrooms (Duet Suite)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
  • 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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
  • Sleeps 2
  • 1 Queen Bed and 1 Single Murphy Bed

View all photos for Suite, 1 Queen Bed with Sofa bed (Brighton)

Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds

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
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

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includes taxes & fees
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About the area

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

  • ‪Brickroom - ‬6 min walk
  • ‪Skout Taphouse & Provisions - ‬6 min walk
  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Greenleaf Restaurant - ‬7 min walk
  • ‪Case Coffee Roasters - ‬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 visit 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 travellers love the helpful staff.

Languages

English

More about this property

VISIBILITY

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

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 cots (infant beds)

Pets

    • Pets not allowed

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms

Parking

    • Free on-site self-parking

Other information

    • Smoke-free property
LOB_HOTELS

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 reception
  • Luggage storage

Facilities

  • 5 buildings/towers
  • Built in 1886
  • Garden
  • Terrace
  • Victorian architecture
ROOM

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 duvet
  • Premium bedding
  • Pillow-top mattress

What to enjoy

  • Individually furnished and decorated

Freshen up

  • Designer toiletries
  • Hairdryer
  • Towels

Stay connected

  • Free WiFi
  • Phone

More

  • Daily housekeeping
MONETIZATION_ON

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or checkout. 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

Optional extras

  • Late checkout can be arranged for an extra charge

Policies

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

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.

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 on-site restaurant.

What's the area around Winchester Inn like?

Winchester Inn is in Historic Downtown District, a short 2-minute walk from Oregon Cabaret Theatre and 4 minutes' walk from Lithia Park.

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Winchester Inn Reviews

Reviews

9.6

Exceptional

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.4/10

Eco-friendliness

Popular mentions

Service staff
Room
Breakfast
Restaurant
Food
Bed
Location
Bathroom
Store
Downtown

What guests liked

  • Breakfast was consistently described as good, plentiful, varied, delicious, and heavenly. (23 reviews)
  • The property's restaurant offered a lovely dining experience with a high-end atmosphere, excellent service, and a heavenly breakfast. (3 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Reviews

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

10/10 Exceptional

Loved our stay so much!
Amy, 2-night trip

10/10 Exceptional

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

10/10 Exceptional

Weekend getaway

The room was amazing, and perfect location . The only negative was how small the tv was but we didn’t end up using it do wasn’t a big deal. The fire place motor sounded like it was on when everything was turned off. The room was amazing and definitely will come back, breakfast was good only bummer was the expresso machine was broken. The bed was comfortable, and staff was great. I love the little touch and personalization in the room.
Heather, 1-night trip

10/10 Exceptional

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

10/10 Exceptional

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
Leonilda, 1-night trip

10/10 Exceptional

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

10/10 Exceptional

Beautiful place to stay
Anita, 1-night trip

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

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

10/10 Exceptional

Beautiful location, friendly staff, amazing stay!
Heather, 1-night trip

10/10 Exceptional

Always a beautiful place to stay!
Chris, 1-night trip

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

10/10 Exceptional

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

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

10/10 Exceptional

Staying at the Winchester Inn is simply stellar beyond compare and it's very convenient to Ashland and walking to the plays.
Donna, 3-night trip

10/10 Exceptional

Loved the luxurious bedding and sweet delivered to the room daily
Linda, 2-night trip

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

10/10 Exceptional

Lovely stay. A very unique experience.
Becki, 2-night trip

10/10 Exceptional

Our stay was great the staff was helpful and on top of everything! Also they have a fabulous restaurant and bar. We enjoyed some evening drinks and if we wanted could take back the drinks to our room. The breakfast was heavenly and the waiter provided top notch service. The room was clean, neat and they proved lovely treats. All in all I will be back.
Monica, 2-night trip

8/10 Very good

Great staff and really clean and comfortable rooms.Love the location and quick walk to local cafe’s and restaurants.
Bradley, 2-night trip

10/10 Exceptional

Loved our stay as always. Breakfast was also delicious.

10/10 Exceptional

cozy is alive and well in ashland

it was cozy and perfect
Robert, 1-night trip

10/10 Exceptional

Love the restaurant!
Robert, 1-night trip

10/10 Exceptional

It is always a treat to stay at The Winchester! Without a doubt, it is my favorite place to stay!
Janet, 4-night trip