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Winchester Inn

3.5 star property
3.5-star Victorian inn near Oregon Shakespeare Festival

Choose dates to view prices

Photo gallery for Winchester Inn

Bar (on property)
Suite, 1 King Bed (Barbara Howard) | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Front of property
Suite, 1 Bedroom (Silverdale) | Living area | Flat-screen TV
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area | Flat-screen TV

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Laundry
  • Bar
  • Housekeeping
  • Air conditioning

Explore the area

Map
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

Room options

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)

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

Double Room, 1 Queen Bed (Marjorie Roy)

  • 350 sq ft
  • 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)

  • 350 sq ft
  • 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)

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

Double Room, 1 King Bed (Andrew G)

  • 400 sq ft
  • 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)

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

Double Room, 1 King Bed (Peter Benjamin)

  • 400 sq ft
  • 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)

  • 400 sq ft
  • 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)

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

Double Room, 1 Queen Bed (Catharine M)

  • 300 sq ft
  • 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)

  • 400 sq ft
  • 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)

  • 900 sq ft
  • 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)

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

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

  • 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) | 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

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

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)

  • 450 sq ft
  • 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)

  • 500 sq ft
  • 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)

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

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

Heart of Ashland.A stay at this Historic Downtown District inn places you steps from Oregon Cabaret Theatre and within a 5-minute walk of Oregon Shakespeare Festival. Ashland Library and Lithia Park are also within half a mile (1 km).
View more Inns in AshlandOpens in a new window

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

3.5-star Victorian inn near Oregon Shakespeare Festival
There's a restaurant on site. You can enjoy a drink at the bar/lounge. Free breakfast is available daily. WiFi is free in public spaces.

A terrace, gift shops/newsstands, and tour/ticket assistance are also featured at Winchester Inn. Free self parking is available.

This Victorian Ashland inn is smoke free.

  • 21 guestrooms or units
  • 3 levels
  • 5 buildings
  • Built in 1886
  • Cooked-to-order breakfast (free)
  • Dry cleaning
  • Front desk (limited hours)
  • Storage area for luggage
  • Tour and ticket information
  • Concierge
  • Terrace
  • Garden
  • Gift shop
  • Newspapers in lobby (free)
  • No smoking on site
  • Bar or lounge
  • 1 conference room
  • Dining venue
Winchester Inn offers 21 air-conditioned accommodations with minibars and coffee/tea makers. Each accommodation is individually furnished and decorated. Pillowtop beds feature Egyptian cotton sheets, down comforters, and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries, and hair dryers. Guests can surf the web using the complimentary wireless Internet access. Additionally, rooms include irons/ironing boards and fans. Housekeeping is offered daily and hypo-allergenic bedding can be requested.

Languages

English

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4.7 out of 5, Exceptional, 1,005 reviews
$208 nightly
The price is $232
Jun 23 - Jun 24
Total includes taxes and fees
Ashland Springs Hotel

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

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)

Room amenities

Entertainment

  • Flat-screen TV with cable channels

Bedroom

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

Bathroom

  • Bathrobes
  • Designer toiletries
  • Hair dryer
  • Towels provided

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 staffed during limited hours

Access methods

Front desk (limited hours)

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Cribs (infant beds) are not available.

Property payment types

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • City/local tax: USD 9.0
  • 3 percent destination fee will be charged
  • Administrative fee: USD 6.00 per accommodation, per night

We've listed all charges provided to us by the property.

Optional extras

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

  • A late check-out fee will be charged

This may not be a comprehensive list. Fees and deposits are subject to change and might not include tax.

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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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. This property accepts Visa, Mastercard, American Express, and Discover. Cash is not accepted. 

We should mention

  • Registered guests are the only ones allowed to be in 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

How close is Winchester Inn to the airport?

Winchester Inn is 15.7 mi (22-min drive) away from the Rogue Valley Intl. Airport (MFR) airport, the closest popular airport to the property.

How much does it cost to stay at Winchester Inn?

As of Jun 18, 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on Jun 27, 2025 start from $617.63, 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.

Does Winchester Inn have an airport shuttle?

Airport shuttle services are not available at Winchester Inn.

Does Winchester Inn offer free breakfast?

Winchester Inn offers free cooked-to-order breakfast every day from 8 AM to 9:30 AM.

Is there a casino at Winchester Inn?

No, there is no casino at this inn.

What time is check-in at Winchester Inn?

Check-in start time: 4:00 PM; Check-in end time: 9 PM.

Is there free parking at Winchester Inn?

This inn offers free self parking.

Does Winchester Inn have a pool?

Winchester Inn does not have a pool.

Does Winchester Inn have a restaurant?

Yes, there is a restaurant on site.

Does Winchester Inn have a spa?

There are no spa services available at this inn.

How close is Winchester Inn to downtown Ashland?

Winchester Inn is 0.2 mi away from Ashland.

Winchester Inn Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 211 out of 246 reviews
Rating 8 - Good. 27 out of 246 reviews
Rating 6 - Okay. 3 out of 246 reviews
Rating 4 - Poor. 3 out of 246 reviews
Rating 2 - Terrible. 2 out of 246 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

Amy

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

10/10 Excellent

Kathleen

Business traveler
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

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

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Jan 2025

10/10 Excellent

Diana

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

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

Beautiful and unique

Stayed 1 night in Dec 2024

10/10 Excellent

Leonilda

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
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

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
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

Disliked: Property conditions & facilities, room comfort
Stayed 4 nights in Dec 2024

10/10 Excellent

Rob

Traveled with partner
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
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

8/10 Good

Janet

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

Leonilda

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