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Winchester Inn

3.5 star property
your current months are December, 2024 and January, 2025.
December 2024
January 2025

Photo gallery for Winchester Inn

Front of property
Suite, 1 King Bed (Barbara Howard)
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area
Double Room, 1 King Bed (Eastlake)
Suite, 2 Bedrooms (Duet Suite) | Living area

Reviews

9.8 out of 10

Exceptional

Popular amenities

  • Laundry
  • Bar
  • Housekeeping
  • Air conditioning
  • Parking included

Explore the area

Map
35 S. 2nd St., Ashland, OR, 97520
  • Oregon Cabaret Theatre
    2 min walk
  • Ashland Library
    3 min walk
  • Lithia Park
    4 min walk
  • Ashland, OR (AHM-Sumner Parker Field)
    9 min drive

Room options

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

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio)

  • 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)

  • 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)

  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

  • 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)

  • 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)

  • 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)

  • 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)

  • 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)

  • 33 sq m
  • 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)

  • 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)

  • 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)

  • 84 sq m
  • 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)

  • 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)

  • 46 sq m
  • 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)

  • 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)

Suite, 1 Queen Bed with Sofa bed (Courtyard)

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)

Suite, 1 King Bed (Fordyce)

Suite, 1 King Bed (Fordyce)

  • 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)

  • 46 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

  • 42 sq m
  • 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)

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

Similar properties

Exterior

Ashland Springs Hotel

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Spa
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Parking included
4.7 out of 5, Exceptional, (1002)
The price is NZ$250
for 1 night
includes taxes & fees
5 Jan - 6 Jan
Ashland Springs Hotel

About the area

Ashland

A stay at Winchester Inn places you in the heart of Ashland, steps from Oregon Cabaret Theatre and 3 minutes by foot from Ashland Library. .This inn is 0.2 mi (0.3 km) from Lithia Park and 0.2 mi (0.3 km) from Oregon Shakespeare Festival.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 2 min walk
  • Ashland Library - 3 min walk
  • Lithia Park - 4 min walk
  • Oregon Shakespeare Festival - 4 min walk
  • Southern Oregon University - 16 min walk

Getting around

  • Rogue Valley Intl. Airport (MFR) - 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

Victorian Ashland inn in Historic Downtown District with free breakfast
Winchester Inn offers 21 air-conditioned accommodations with minibars and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Make yourself at home in one of the 21 individually decorated guestrooms, featuring minibars and flat-screen televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have designer toiletries and hair dryers.
Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional amenities at this Victorian inn include concierge services and gift shops/newsstands.
At Winchester Inn, enjoy a satisfying meal at the restaurant. Quench your thirst with your favorite drink at the bar/lounge. A complimentary cooked-to-order breakfast is served daily from 8 AM to 9:30 AM.
Featured amenities include complimentary newspapers in the lobby, dry cleaning/laundry services, and luggage storage. Free self parking is available onsite.
A complimentary cooked-to-order breakfast is served each morning between 8 AM and 9:30 AM.
Winchester Inn has a restaurant on site.

Languages

English

Property amenities

Internet

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

Parking and public transport

  • Free self-parking on site

Food and drink

  • Free cooked-to-order breakfast available daily 8 AM–9:30 AM
  • 1 restaurant
  • 1 bar

Conveniences

  • Free newspapers in reception
  • Gift shop/newsstand

Guest services

  • Concierge services
  • Daily housekeeping
  • Dry-cleaning service
  • Front desk (limited hours)
  • Luggage storage
  • Tour/ticket assistance

Business services

  • A meeting room

Outdoors

  • Garden
  • Terrace

Accessibility

  • If you have any requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • This property does not have any lifts
  • Wheelchair-accessible (may have limits)

More

  • Smoke-free property

Room amenities

Bedroom

  • Air conditioning
  • Bed sheets
  • Down duvet
  • Egyptian cotton sheets
  • Fan
  • Heating
  • Hypo-allergenic bedding
  • Pillow-top mattress
  • Premium bedding

Bathroom

  • Dressing gowns
  • Designer toiletries
  • Hairdryer
  • Towels

Entertainment

  • TV channels
  • Flat-screen TV

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Individually decorated
  • Individually furnished
  • 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
Cribs (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:

  • City/local tax: USD 9.0
  • 3 percent tourism 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

We should mention

This property does not have elevators
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

Winchester Inn Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 198 out of 230 reviews" "
Rating 8 - Good. 25 out of 230 reviews" "
Rating 6 - Okay. 3 out of 230 reviews" "
Rating 4 - Poor. 2 out of 230 reviews" "
Rating 2 - Terrible. 2 out of 230 reviews" "

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.6/10

Eco-friendliness

Reviews

10/10 Excellent

Gregory

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful
Stayed 2 nights in Sep 2024

6/10 Okay

Robert, Portland

Travelled with partner
Liked: Cleanliness, staff & service, amenities
Disliked: Property conditions & facilities
The heating/cooling are awful. Some maintenance needs to be done. Takes forever to get hot water. Sink drains are slow. The breakfasts are fantastic! Still, we won't be going back.
Stayed 5 nights in Sep 2024

10/10 Excellent

Larry, Moraga

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

Leonilda

Stayed 1 night in Aug 2024

10/10 Excellent

Linda

Travelled with partner
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

Gregory, Carefree

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful, extremely well maintained property in the heart of Ashland with lots of character and deluxe amenities. Very friendly and helpful staff. Gourmet restaurant on premises and superb breakfast with many options. Walk to everything. Highly recommend.
Stayed 1 night in Aug 2024

10/10 Excellent

Christine

Travelled with partner
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

10/10 Excellent

Kathryn

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfection
Room very nice. Great location. Delicious food.
Stayed 2 nights in Jul 2024

10/10 Excellent

james

Stayed 1 night in Jul 2024

10/10 Excellent

Larry, Moraga

Travelled with partner
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

10/10 Excellent

Gregg

Stayed 1 night in Jun 2024

10/10 Excellent

Kevin, Astoria

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

10/10 Excellent

Jody

Travelled with partner
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

8/10 Good

Robert, Portland

Travelled with partner
Liked: Cleanliness, staff & service, amenities
The food is amazing! Unfortunately, there are many things that should be fixed or upgraded. For the price, it should be in perfect condition.
Stayed 3 nights 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

Robert

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
cozy is alive and well in ashland
it was cozy and perfect
Stayed 1 night in Jun 2024

10/10 Excellent

Starlyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The Winchester is idealic. Its so quaint and pretty. They thought of every detail down to a personal greeting in the room and reservations for their complimentary breakfast, which was like eating at a high end restaurant, and the bed is made by the time you return. The room was so clean, and the towels and bedding were really high quality. And the staff were fantastic! I really look forward to staying here again
Stayed 2 nights in Jun 2024

10/10 Excellent

Linda

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Jun 2024

6/10 Okay

Robert

Stayed 1 night in May 2024

10/10 Excellent

Derek

Travelled with family
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 4 nights in Jun 2024

10/10 Excellent

Kathryn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This was a lovely stopover in Ashland on our way to Santa Barbara. It is a charming, well run inn. This was Memorial Day weekend so breakfast was not “full service” but what we had was delicious.
Stayed 1 night in May 2024

4/10 Poor

Karen

Business traveller
Liked: Cleanliness, amenities, property conditions & facilities
Disliked: Staff & service
I booked the Garden Room for a Queen bed and a sofa bed. I even asked again when I was shown the room if the sofa made into a bed and ahead of time asked to be sure there would be extra bedding for the sofa bed. I was assured upon check in that the sofa made into a bed. It does not. The Queen is more of a double than a Queen and the other guest had to sleep in the bay window minus extra bedding. I tried to get help by calling front desk, no answer. The dishwasher offered his condolences, the staff are nice, but this is poor service to not be able to reach anyone for help in the evening. Very disappointed.
Stayed 1 night in May 2024

10/10 Excellent

Bonnie J

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

8/10 Good

Robert, Portland

Travelled with partner
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

10/10 Excellent

Patricia

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We loved everything about this inn!
Stayed 1 night in Apr 2024