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Winchester Inn

3.5 star property

Choose dates to view prices

Photo gallery for Winchester Inn

Front of property
Suite, 1 King Bed (Hargadine) | Bathroom shower
Family Suite, City View | Living area | Flat-screen TV
Bar (on property)
Suite, 1 King Bed (Hargadine) | Living room | Flat-screen TV

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services

Explore the area

View in a map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Cabaret Theatre
    ‪1 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Place, Lithia Park
    ‪3 min walk‬
  • Airport, Medford, OR (MFR-Rogue Valley Intl.)
    ‪23 min drive‬

Room options

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)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

9.6 out of 10
Exceptional
(5 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Bed
  • Free WiFi

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)

9.4 out of 10
Exceptional
(3 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(5 reviews)
  • 300 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(2 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(3 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(1 review)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

7.0 out of 10
Good
(2 reviews)
  • 500 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

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)

  • 700 sq ft
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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)

  • 900 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

  • 500 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

9.0 out of 10
Wonderful
(2 reviews)
  • 500 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)

8.0 out of 10
Very good
(1 review)
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Twin Murphy Bed
  • Free WiFi

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)

  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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)

  • 450 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

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)

10.0 out of 10
Exceptional
(1 review)
  • 450 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

View all photos for Suite, Garden View

Suite, Garden View | Living area | Flat-screen TV

Suite, Garden View

  • Garden view
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free WiFi

View all photos for Family Suite, City View

Family Suite, City View | Living area | Flat-screen TV

Family Suite, City View

  • City view
  • 850 sq ft
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Twin Bed
  • Free WiFi

View all photos for Superior Suite, Mountain View

Superior Suite, Mountain View | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Superior Suite, Mountain View

  • Mountain view
  • 500 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free WiFi

About the neighborhood

Ashland

Located in Historic Downtown District, Winchester Inn is adjacent to Oregon Cabaret Theatre and within a 5-minute walk of Oregon Shakespeare Festival. This 21-room, 3.5-star inn welcomes guests with free breakfast, free in-room WiFi, and free self parking.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 1 min walk - 0.1 miles
  • Oregon Shakespeare Festival - 3 min walk - 0.2 miles
  • Lithia Park - 3 min walk - 0.2 miles
  • Allen Elizabethan Theatre - 5 min walk - 0.3 miles
  • Angus Bowmer Theatre - 5 min walk - 0.3 miles

Getting around

  • Rogue Valley Intl. Airport (MFR) - 22 min drive

Restaurants

  • ‪Martolli's Hand Tossed Pizza - ‬5 min walk
  • ‪Case Coffee Roasters - ‬6 min walk
  • ‪Skout Taphouse & Provisions - ‬6 min walk
  • ‪Zoey's Cafe - ‬3 min walk
  • ‪Ruby's - ‬6 min walk

About this property

Winchester Inn

Guests of Winchester Inn enjoy free WiFi in public areas, a meeting room, and free newspapers. If you plan to drive, free parking is available. Front-desk staff can assist with luggage storage, dry cleaning/laundry, and tours or tickets. Additional amenities include a terrace, a garden, and a gift shop.
Guests can expect to find free WiFi and flat-screen TVs with cable channels. Bathrooms offer hair dryers and designer toiletries, and pillowtop beds with Egyptian cotton sheets and down comforters ensure a restful night. Minibars, coffee makers, and phones are also standard.

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Jun 7 - Jun 8
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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

  • Hardwood flooring in room
  • High-pile carpet in room
  • No elevator

More

  • 3 floors
  • 5 buildings
  • Built in 1886
  • Smoking not allowed
  • Victorian architecture

Room amenities

Bedroom

  • Down comforter
  • Egyptian cotton sheets
  • Hypo-allergenic bedding
  • Pillowtop mattress

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Connecting rooms available
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop workspace
  • 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
Information provided by the property may be translated using automated translation tools

Access methods

Front desk (limited hours)

Pets

  • This property doesn't allow pets

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

  • A tax is imposed by the city: USD 9
  • 4 percent destination fee will be charged
  • Administrative fee: USD 10.00 per accommodation, per night

These are all of the charges provided to us by the property.

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

  • A late check-out fee will be charged

This list may not be comprehensive. Fees and deposits might 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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
  • Check-in: 4:00 PM
  • Check-out: 11 AM
  • Minimum check-in age: 21
The front desk is available during limited hours. Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards. Cash is not accepted. 
  • Onsite safety features include a fire extinguisher.

Additional information about polices, regulations, and more:

  • Registered guests are the only ones allowed in guestrooms.
  • Connecting or adjoining rooms can be requested, but all rooms are subject to availability. Contact the property using the phone number on your booking confirmation.
  • There are no elevators.
  • No cribs or infant beds are available.

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

What's there to do near Winchester Inn?

This inn is situated in Historic Downtown District, just steps from Oregon Shakespeare Festival and Oregon Cabaret Theatre, and within a short walk of Lithia Park. You'll also find Angus Bowmer Theatre and Allen Elizabethan Theatre less than a mile away.

How much does it cost to stay at Winchester Inn?

As of Jun 6, 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on Jun 8, 2026 start from $279, including 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.

Is there parking available at Winchester Inn?

Yes, self parking is offered for free at the inn.

Does Winchester Inn have a casino on the premises?

No, Winchester Inn doesn't have a casino.

Is there an indoor pool at Winchester Inn?

No, there is no indoor pool at this inn.

Is Winchester Inn good for couples?

There are many amenities for couples at this inn, including a restaurant and a bar/lounge plus some guestrooms feature a fireplace.

Are there hot tubs at Winchester Inn?

No, but some guestrooms at this inn feature jetted bathtubs.

Does Winchester Inn have a restaurant with a breakfast menu?

Yes, Winchester Inn serves free cooked-to-order breakfasts each morning from its restaurant.

Does Winchester Inn allow pets to stay free of charge?

No, pets aren't allowed at Winchester Inn.

Are there connecting rooms at Winchester Inn?

Yes, this inn has connecting rooms you can book for your group event or vacation.

Where is the closest airport to Winchester Inn?

The closest major airport to Winchester Inn is Rogue Valley Intl. Airport (MFR), which is 15.7 mi away (22 minutes by car).

Are there rooms with balconies at Winchester Inn?

Yes, some guestrooms at this inn offer either a furnished balcony and a furnished patio where guests can enjoy mountain and garden views.

Winchester Inn Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 237 out of 275 reviews
Rating 8 - Good. 28 out of 275 reviews
Rating 6 - Okay. 4 out of 275 reviews
Rating 4 - Poor. 3 out of 275 reviews
Rating 2 - Terrible. 3 out of 275 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.6/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Willy

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful B&B. This will now be our favorite stop in Ashland.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Laura

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Super comfortable room, great location to Main Street, excellent check in with friendly staff, would definitely stay here again!
Stayed 1 night in Sep 2025
Verified

10/10 Excellent

Stacey

Liked: Cleanliness, amenities, property conditions & facilities
The room is fantastic!! Highly recommend!
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Amy

Liked: Amenities, property conditions & facilities
Loved our stay so much!
Stayed 2 nights in Feb 2025
Verified

10/10 Excellent

Carolyn

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful room with comfortable bed. Nice quality bedding.
Stayed 1 night in Oct 2025
Verified

8/10 Good

James

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Property was beautiful. Room was large, clean and nicely appointed. The only disappointment was not getting to sample the highly rated breakfast as we learned after we made our booking that the kitchen and restaurant were shut down for a yearly deep clean.
Stayed 1 night in Jan 2026
Verified

10/10 Excellent

Dirk

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful property, really comfortable bed, pillows and sheets!
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Anita

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

10/10 Excellent

Heather

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

10/10 Excellent

Chris

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

10/10 Excellent

Patricia

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

10/10 Excellent

Christi

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Such a unique Victorian place! So charming, clean and spacious….
Stayed 2 nights in Aug 2025
Verified

10/10 Excellent

Patricia

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Lovely room
Stayed 1 night in Oct 2025
Verified

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
Verified

2/10 Terrible

Mei

Disliked: Cleanliness, amenities, property conditions & facilities
Why it calls itself hotel really puzzles me. Very dated dirty carpet, loud split heating/ac, not to mention nobody checks you in at 11pm with poor instructions. Will NEVER stay here.
Stayed 1 night in Dec 2025
Verified

8/10 Good

Bradley

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great staff and really clean and comfortable rooms.Love the location and quick walk to local cafe’s and restaurants.
Stayed 2 nights in Oct 2022
Verified

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
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Great inn. Maintained beautifully. Excellent service from staff, who make guests very comfortable.
Stayed 2 nights in Apr 2025
Verified

10/10 Excellent

Nick

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
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.
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Charlotte

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Loved our stay as always. Breakfast was also delicious.
Verified

10/10 Excellent

Ellen

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

10/10 Excellent

Mary

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Excellent satff that made our stay a pleasure.
Stayed 1 night in Oct 2023
Verified

10/10 Excellent

Aaron

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Exceptionally friendly and helpful staff; room was beautiful and clean; one block from many restaurants and shopping.
Verified

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
Verified

10/10 Excellent

Robert

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Love the restaurant!
Stayed 1 night in Mar 2022

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