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Winchester Inn

3.5 star property
Comfortable Victorian inn, walk to Oregon Shakespeare Festival

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your current months are May, 2024 and June, 2024.
May 2024
June 2024

Photo gallery for Winchester Inn

Front of property
Double Room, 1 Queen Bed (Patio) | Terrace/patio
Double Room, 1 King Bed (Enders)
Suite, 1 Queen Bed with Sofa bed (Courtyard)
Double Room, 1 King Bed (Eastlake)
Reviews
9.8

Exceptional

Popular amenities

  • Breakfast included
  • Parking includedParking includedParking included
  • Free WiFiFree WiFiFree WiFi
  • LaundryLaundryLaundry
  • Restaurant
  • BarBarBar
The price is CA $306
CA $342 total
includes taxes & fees
26 May - 27 May

Check out the area

Map
35 S. 2nd St., Ashland, OR, 97520
  • Popular LocationOregon Shakespeare Festival4 min walk
  • Popular LocationAllen Elizabethan Theatre5 min walk
  • Popular LocationSouthern Oregon University16 min walk
  • AirportMedford, OR (MFR-Rogue Valley Intl.)21 min drive

Most relevant reviews

ExperimentalCarousel

10/10 Excellent

My only complaint was the patio room is located below staff work area and very noisy until 10 pm.
Kelly
Nov. 2, 2022
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Room options

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

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio)

Highlights

Furnished patio
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 350 sq ft
  • 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
Pillowtop bed
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Bedroom (Garden)

Double Room, 1 Bedroom (Garden)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Separate bedroom
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
  • 350 sq ft
  • 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)

Highlights

Furnished balcony
Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 400 sq ft
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
  • 350 sq ft
  • 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
  • 400 sq ft
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed

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

Double Room, 1 Bedroom (Sylvan)

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
  • 350 sq ft
  • 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)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillowtop bed
  • 300 sq ft
  • 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)

Highlights

Furnished balcony
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 400 sq ft
  • 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
  • 900 sq ft
  • 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
  • 500 sq ft
  • 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)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 500 sq ft
  • 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
  • 700 sq ft
  • 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
  • 450 sq ft
  • 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)

Highlights

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

Highlights

Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
  • 500 sq ft
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

Highlights

Separate sitting area
Individually furnished
Individually decorated
Fireplace
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
  • 450 sq ft
  • 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
  • 450 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

Similar properties

Lobby
The Bard's Inn, BW Signature Collection by Best Western
Pool
Breakfast included
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Parking included
8.8 out of 10, Excellent, (1000)
The price is CA $205
CA $228 total
includes taxes & fees
May 19 - May 20
The Bard's Inn, BW Signature Collection by Best Western

About the area

Ashland

Winchester Inn is located in Historic Downtown District, a neighborhood in Ashland, and 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

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

  • Skout Taphouse & Provisions - 6 min walk
  • Gil's - 6 min walk
  • The Growler Guys - 3 min walk
  • Martolli's Hand Tossed Pizza - 5 min walk
  • Brickroom - 6 min walk

About this property

Winchester Inn

Inn located in Historic Downtown District
Oregon Shakespeare Festival is located near Winchester Inn, which provides free cooked-to-order breakfast, a terrace, and a garden. 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
  • Concierge services, tour/ticket assistance, and 1 meeting room
  • Luggage storage, smoke-free premises, and free newspapers
  • Guest reviews give top marks for the breakfast and 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
  • Electric kettles, daily housekeeping, and phones

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 8:00 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 elevator
  • 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

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Towels

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 staff will greet guests on arrival

Access methods

Staffed front desk

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:

  • City/local tax: USD 9.0
  • 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 does it cost to stay at Winchester Inn?

As of May 15, 2024, prices found for a 1-night stay for 2 adults at Winchester Inn on May 26, 2024 start from CA $306.49, excluding 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?

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 and Oregon Shakespeare Festival. Ashland Library and Lithia Park are also within 5 minutes.

Winchester Inn Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 175 out of 203 reviews" "
Rating 8 - Good. 23 out of 203 reviews" "
Rating 6 - Okay. 1 out of 203 reviews" "
Rating 4 - Poor. 2 out of 203 reviews" "
Rating 2 - Terrible. 2 out of 203 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

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

8/10 Good

Huong, Kirkland

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Mar 2024

10/10 Excellent

Hong

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room looks very nice. The hotel is in downtown, within walking distance to a few dinning options. It is very continent. The staff is nice. We’d love to stay again!
Stayed 1 night in Jan 2024

10/10 Excellent

Sarah

Stayed 1 night in Jan 2024

10/10 Excellent

carolyn

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wonderful
Amazing room with a balcony, fire place, comfy bed and beautiful walk in shower. It was so nice having a beautiful restaurant down stairs.
Cozy and able to stream to the TV
So comfortable
Stayed 1 night in Dec 2023

10/10 Excellent

Ellen

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

10/10 Excellent

Kari

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing!!
I came here on a solo vacation and everyone was absolutely amazing the entire time I was there! The inn itself was absolutely beautiful and the food was so delicious!! I will definitely be back!!
Stayed 2 nights in Nov 2023