Winchester Inn

Victorian inn with free breakfast and a restaurant

Choose dates to view prices

Where to?

Dates

August 2025

September 2025

Enjoy a drink at the bar, surrounded by lush views and comfortable seating.

Relax in a classic, elegantly decorated room with a four-poster bed and comfortable seating area.

Enjoy cooking in this well-equipped kitchen with a dishwasher and sink.

Traditional Victorian-style house with a wrap-around balcony and well-maintained garden.

Relax in this inviting living area with a sofa, chair, and table, offering a peaceful escape.

Overview
Rooms
Location
Policies

Popular amenities

Laundry
Bar
Housekeeping
Air conditioning

Explore the area

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

Oregon Shakespeare Festival
‪3 min walk‬
Lithia Park
‪3 min walk‬
Southern Oregon University
‪17 min walk‬
Medford, OR (MFR-Rogue Valley Intl.)
‪25 min drive‬

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Room options

Double Room, 1 Queen Bed (Patio)

Exceptional

350 sq ft
Sleeps 2
1 Queen Bed

Double Room, 1 Queen Bed (Marjorie Roy)

350 sq ft
Sleeps 2
1 Queen Bed

Double Room, 1 Bedroom (Garden)

Exceptional

350 sq ft
Sleeps 2
1 Queen Bed

Double Room (Queen Anne)

Exceptional

350 sq ft
Sleeps 2
1 Queen Bed and 1 Twin Bed

Double Room, 1 King Bed (Andrew G)

Exceptional

400 sq ft
Sleeps 2
1 King Bed

Double Room, 1 King Bed (Eastlake)

Exceptional

350 sq ft
Sleeps 2
1 King Bed

Double Room, 1 King Bed (Peter Benjamin)

400 sq ft
Sleeps 2
1 King Bed

Double Room, 1 King Bed (Enders)

Exceptional

400 sq ft
Sleeps 2
1 King Bed

Double Room, 1 Bedroom (Sylvan)

Exceptional

350 sq ft
Sleeps 2
1 Queen Bed and 1 Double Sofa Bed

Double Room, 1 Queen Bed (Catharine M)

Exceptional

300 sq ft
Sleeps 2
1 Queen Bed

Double Room, 1 King Bed (Sunset)

Exceptional

400 sq ft
Sleeps 2
1 King Bed

Suite, 1 King Bed (Hargadine)

900 sq ft
Sleeps 2
1 King Bed

Suite, 1 King Bed (Barbara Howard)

500 sq ft
Sleeps 2
1 King Bed

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

Good

500 sq ft
Sleeps 2
1 King Bed and 1 Double Sofa Bed

Suite, 2 Bedrooms (Duet Suite)

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

Suite, 1 Queen Bed with Sofa bed (Courtyard)

450 sq ft
Sleeps 2
1 Queen Bed and 1 Double Sofa Bed

Suite, 1 King Bed (Fordyce)

Exceptional

450 sq ft
Sleeps 2
1 King Bed

Suite, 1 King Bed (Eleanor Rose)

Wonderful

500 sq ft
Sleeps 2
1 King Bed

Suite, 1 Bedroom (Silverdale)

Very good

450 sq ft
Sleeps 2
1 Queen Bed and 1 Twin Murphy Bed

Suite, 1 Queen Bed with Sofa bed (Brighton)

450 sq ft
Sleeps 2
1 Queen Bed and 1 Double Sofa Bed

About the neighborhood

Ashland

Located in Historic Downtown District, Winchester Inn is adjacent to Oregon Cabaret Theatre and within a 5-minute walk of Ashland Library. This 21-room, 3.5-star inn welcomes guests with free breakfast, free in-room WiFi, and free self parking.

View more Inns in Ashland

What's nearby

Oregon Cabaret Theatre - 1 min walk - 0.0 miles
Allen Elizabethan Theatre - 3 min walk - 0.2 miles
Oregon Shakespeare Festival - 3 min walk - 0.2 miles
Lithia Park - 3 min walk - 0.2 miles
Southern Oregon University - 17 min walk - 0.9 miles

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 inn with free breakfast and a restaurant

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 fans are also standard.

Languages

English

Similar properties

Relax in a serene outdoor space surrounded by lush greenery and warm lighting.

Spa
Pet friendly
Parking included
Free WiFi

$183 nightly

Aug 10 - Aug 11

Total includes taxes and fees

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)

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
Towels provided

Entertainment

Flat-screen TV with cable channels

Food and drink

Coffee/tea maker
Electric kettle
Minibar

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 staffed during limited hours

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 9.0
3 percent destination fee will be charged
Administrative fee: USD 6.00 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

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.

Additional information about polices, regulations, and more:

Registered guests are the only ones allowed in guestrooms.
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 Cabaret Theatre and Ashland Library, and within a short walk of Lithia Park. You'll also find Oregon Shakespeare Festival and Allen Elizabethan Theatre less than a mile away.

Is parking available on site 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.

What will couples enjoy most about a stay at Winchester Inn?

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

Are there hot tubs at Winchester Inn?

No, but this inn offers jetted bathtubs in some guestrooms.

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?

No, this inn doesn't feature connecting guestrooms.

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).

Can I book a room with a balcony at Winchester Inn?

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

Winchester Inn Reviews

9.6

Exceptional

9.8/10

Cleanliness

9.8/10

Staff & service

9.6/10

Amenities

9.6/10

Property conditions & facilities

9.4/10

Eco-friendliness

10/10 Excellent

Thomas

Apr 27, 2025

Stayed 1 night in Mar 2025

10/10 Excellent

Verified traveler

Apr 21, 2025

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

10/10 Excellent

Raul

Mar 27, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 3 nights in Mar 2025

10/10 Excellent

Amy

Traveled with partner

Mar 19, 2025

Liked: Amenities, property conditions & facilities

Loved our stay so much!

Stayed 2 nights in Feb 2025

10/10 Excellent

Kathleen

Business traveler

Feb 21, 2025

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

Leonilda

Feb 1, 2025

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great and beautiful place to stay. Delicious brea

Stayed 1 night in Jan 2025

10/10 Excellent

Donna

Jan 21, 2025

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 1 night in Jan 2025

10/10 Excellent

Diana

Jan 20, 2025

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Wonderful

The Winchester, especially the Hargadine Suite, is the best hotel on the west coast. I love it so much it is a very very uniquely special place. I go to Ashland specifically for the Winchester and their amazing breakfast.

Stayed 2 nights in Jan 2025

10/10 Excellent

Leonilda

Jan 18, 2025

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Beautiful and unique

Stayed 1 night in Dec 2024

10/10 Excellent

Leonilda

Jan 17, 2025

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Friendly, comfortable & unique place to enjoy

Great beautiful Inn with unique rooms. Delicious breakfast nenu with gluten-free items that are wonderful and I so enjoy

Stayed 1 night in Jan 2025

10/10 Excellent

Monica

Traveled with partner

Jan 14, 2025

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

Verified traveler

Jan 5, 2025

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Stayed 1 night in Dec 2024

8/10 Good

Rebecca A

Business traveler, Traveled with family

Jan 3, 2025

Liked: Staff & service, property conditions & facilities, room comfort

Great place, but.....

The place and staff is fabulous. Always like it. Sorry to say I have the same complaint now as last time we were there, and we stayed in a different room. The carpets were filthy. Even if they were clean, they looked horrible with all the stains. How about hard wood floors or..... Thanks for listening.

Stayed 1 night in Dec 2024

4/10 Poor

Anna

Jan 1, 2025

Disliked: Property conditions & facilities, room comfort

Stayed 4 nights in Dec 2024

10/10 Excellent

Rob

Traveled with partner

Nov 3, 2024

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

Robin

Traveled with partner

Oct 24, 2024

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

Oct 24, 2024

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

Oct 15, 2024

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

Oct 7, 2024

Lovely stay. A very unique experience.

Stayed 2 nights in Oct 2024

8/10 Good

Janet

Sep 30, 2024

Liked: Cleanliness, staff & service, property conditions & facilities

Stayed 1 night in Jul 2024

10/10 Excellent

Gregory

Sep 21, 2024

Liked: Cleanliness, staff & service, amenities, property conditions & facilities

Beautiful

Stayed 2 nights in Sep 2024

6/10 Okay

Robert, Portland

Traveled with partner

Sep 19, 2024

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