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Winchester Inn

3.5 star property
Victorian Ashland inn in Historic Downtown District with free breakfast

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Photo gallery for Winchester Inn

Front of property
Suite, 2 Bedrooms (Duet Suite) | Living area | Flat-screen TV
Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Double Room, 1 King Bed (Eastlake) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area | Flat-screen TV

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Breakfast included
  • Laundry
  • Bar
  • Housekeeping
  • Air conditioning
  • Parking included
The current price is AED 405
AED 486 total
includes taxes & fees
3 Mar - 4 Mar

Room options

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Patio)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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
Premium bedding
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Bedroom (Garden) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Bedroom (Garden)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton linens
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room (Queen Anne)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Andrew G)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Eastlake)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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)

Double Room, 1 King Bed (Enders) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Enders)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Bedroom (Sylvan)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Separate bedroom
  • 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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 Queen Bed (Catharine M)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Double Room, 1 King Bed (Sunset)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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)

Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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)

Suite, 1 King Bed with Sofa bed (Robert Gordon) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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

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)

Suite, 2 Bedrooms (Duet Suite) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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)

Suite, 1 Queen Bed with Sofa bed (Courtyard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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)

Suite, 1 King Bed (Fordyce) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Fordyce)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 King Bed (Eleanor Rose)

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) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Suite, 1 Bedroom (Silverdale)

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 Twin Murphy Bed

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

Suite, 1 Queen Bed with Sofa bed (Brighton) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop 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

Similar properties

Exterior

Ashland Springs Hotel

  • Breakfast included
  • Spa
  • Pet friendly
  • Parking included
9.4 out of 10, Exceptional, (1001)
The price is AED 534
AED 614 total
includes taxes & fees
23 Feb - 24 Feb
Ashland Springs Hotel

About the neighborhood

Map
35 S. 2nd St., Ashland, OR, 97520

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

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 like:
  • Free self parking
  • 1 meeting room, smoke-free premises, and a gift shop
  • Concierge services, tour/ticket assistance, and luggage storage
  • Guest reviews give top marks for the helpful staff
Room features
All guestrooms are individually furnished, and feature comforts such as premium bedding and air conditioning, in addition to thoughtful touches like free WiFi and bathrobes.
Extra conveniences in all rooms include:
  • Heating and fans
  • Hypo-allergenic bedding, Egyptian cotton sheets, and pillowtop mattresses
  • Designer toiletries and hair dryers
  • Flat-screen TVs with cable channels
  • Wardrobes/closets, electric kettles, and daily housekeeping

Languages

English

Property amenities

Internet

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

Parking and transportation

  • 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 lobby
  • Gift shop/newsstand

Guest services

  • Concierge services
  • Daily housekeeping
  • Dry cleaning service
  • Front desk (limited hours)
  • Luggage storage
  • Tour/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.
  • This property does not have elevators
  • Wheelchair accessible (may have limitations)

More

  • Smoke-free property

Room amenities

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Towels

Entertainment

  • Cable 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

Property 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

Frequently asked questions

Is Winchester Inn pet-friendly?

No, pets are not allowed at this property.

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?

Check-out is at 11 AM. Late check-out 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

9.6

Exceptional

Rating 10 - Excellent. 206 out of 240 reviews
Rating 8 - Good. 26 out of 240 reviews
Rating 6 - Okay. 3 out of 240 reviews
Rating 4 - Poor. 3 out of 240 reviews
Rating 2 - Terrible. 2 out of 240 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

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

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

Monica

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

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

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

10/10 Excellent

Becki

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

10/10 Excellent

Patricia

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

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

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

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

Anita

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

10/10 Excellent

Robin

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely hotel in downtown Ashland. High end restaurant attached with lovely bar, as well as outdoor seating options. Walkable to all things in downtown. Stairs required up to room. Large comfortable room. Very nice breakfast. Overall, hotel is expensive, but nice. We really enjoy the restaurant.
Stayed 1 night in Sep 2024

10/10 Excellent

Gregory

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

10/10 Excellent

Christine

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

Heather

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

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

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

Chris

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

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

Jody

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

10/10 Excellent

Larry

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

Ellen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Breakfast was amazing!
Stayed 1 night in Dec 2023

8/10 Good

Robert

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

Bonnie J

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