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Winchester Inn

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

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your current months are November, 2024 and December, 2024.
November 2024
December 2024

Photo gallery for Winchester Inn

Front of property
Double Room, 1 Queen Bed (Patio) | Terrace/patio
Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Bar (on property)
Suite, 1 King Bed (Hargadine) | Bathroom shower

Reviews

9.8 out of 10

Exceptional

Popular amenities

  • Breakfast included
  • Bar
    Bar
  • Laundry
    Laundry
  • Housekeeping
    Housekeeping
  • Air conditioning
    Air conditioning
  • Parking included
    Parking included
The price is SAR 456
Price available on 18/11/2024

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
Pillowtop bed
  • 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
Fan
  • 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, (1005)
The price is SAR 583
SAR 668 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Ashland Springs Hotel

About the neighborhood

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

What's nearby

  • Oregon Cabaret Theatre - 2 min walk
  • Lithia Park - 4 min walk
  • Oregon Shakespeare Festival - 4 min walk
  • Allen Elizabethan Theatre - 5 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
  • Smoke-free premises, a gift shop, and concierge services
  • Free newspapers, luggage storage, and tour/ticket assistance
  • 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

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.

Winchester Inn Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 197 out of 229 reviews" "
Rating 8 - Good. 25 out of 229 reviews" "
Rating 6 - Okay. 3 out of 229 reviews" "
Rating 4 - Poor. 2 out of 229 reviews" "
Rating 2 - Terrible. 2 out of 229 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

Robin

Traveled with partner
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

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

Jennifer

Traveled with partner
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

Becki

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

6/10 Okay

Robert, Portland

Traveled 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

Linda

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

Traveled 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 traveler
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

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