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Winchester Inn

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

Photo gallery for Winchester Inn

Front of property
Suite, 1 Queen Bed with Sofa bed (Courtyard) | Living area
Suite, 2 Bedrooms (Duet Suite) | Living area
Double Room, 1 King Bed (Eastlake)
Suite, 1 King Bed (Barbara Howard)

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Breakfast included
  • Laundry
  • Bar
  • Housekeeping
  • Air conditioning
  • Parking included
The current price is NZ$230
includes taxes & fees
3 Mar - 4 Mar

Explore the area

Map
35 S. 2nd St., Ashland, OR, 97520
  • Oregon Cabaret Theatre
    ‪2 min walk‬
  • Ashland Library
    ‪3 min walk‬
  • Lithia Park
    ‪4 min walk‬
  • Ashland, OR (AHM-Sumner Parker Field)
    ‪9 min drive‬

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

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)

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)

Double Room, 1 Bedroom (Garden)

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Egyptian cotton bed sheets
  • 33 sq m
  • 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
Premium bedding
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Single 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
  • 37 sq m
  • 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
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)

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)

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)

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
  • 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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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 Single 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
  • 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
4.7 out of 5, Exceptional, (1001)
The price is NZ$437
for 1 room
includes taxes & fees
7 Mar - 8 Mar
Ashland Springs Hotel

About the area

Ashland

Winchester Inn places you in the centre of Ashland, steps from Oregon Cabaret Theatre and within a short 5-minute stroll of Ashland Library. Highlights at this Victorian inn include free cooked-to-order breakfast, a restaurant and free self-parking. .The inn's own lounge bar is a nice place to enjoy a drink. Additionally, you'll find free Wi-Fi in public areas, concierge services and a terrace. Each morning free breakfast is served. .Places within a 5-minute walk of this 3.5-property class Historic Downtown District inn include Lithia Park and Oregon Shakespeare Festival.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 2 min walk
  • Ashland Library - 3 min walk
  • Lithia Park - 4 min walk
  • Oregon Shakespeare Festival - 4 min walk
  • Southern Oregon University - 16 min walk

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 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 Ashland inn in Historic Downtown District with free breakfast
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 duvets and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include bathrobes, designer toiletries, complimentary toiletries and hairdryers. Guests can surf the web using complimentary wireless Internet access. Additionally, rooms include an iron/ironing board and fans. Housekeeping is offered on a daily basis and hypo-allergenic bedding can be requested.

Languages

English

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transport

  • Free self parking on site

Food and drink

  • Free cooked-to-order breakfast available daily 8 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 lift
  • Wheelchair accessible (may have limitations)

Room amenities

Bedroom

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

Bathroom

  • Designer toiletries
  • Dressing gowns
  • Hair dryer
  • Towels provided

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 staffed during limited hours

Access methods

Front desk (limited hours)

Pets

  • No pets allowed

Children and extra beds

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

Payment types

Important information

Fees

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

  • City/local tax: USD9.0
  • A 3 per cent tourism 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
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 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

Is parking available at Winchester Inn?

Yep, Winchester Inn has a free self car park.

How much does it cost to stay at Winchester Inn?

As of 21 Feb 2025, prices found for a 1-night stay for 2 adults at Winchester Inn on 3 Mar 2025 start from NZ$213.46, 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.

What makes Winchester Inn a romantic place to stay?

A lounge bar, plus pillowtop beds in the guestrooms, help set the scene for a romantic weekend at Winchester Inn.

Does Winchester Inn serve breakfast?

Yeah, free cooked-to-order breakfast is available daily between 8 AM and 9:30 AM.

Is there a free airport shuttle available at Winchester Inn?

No, Winchester Inn does not offer an airport shuttle service.

Is there a bar or restaurant at Winchester Inn?

Yep, they've got a lounge bar and an onsite restaurant.

What time are check-in & check-out at Winchester Inn?

Check-in begins at 4:00 PM. Check-out time is 11 AM.

Are pets allowed at Winchester Inn?

No, pets are not allowed.

Winchester Inn Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 205 out of 239 reviews
Rating 8 - Good. 26 out of 239 reviews
Rating 6 - Okay. 3 out of 239 reviews
Rating 4 - Poor. 3 out of 239 reviews
Rating 2 - Terrible. 2 out of 239 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

Rob

Travelled 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

Travelled 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

Travelled 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

Travelled 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

10/10 Excellent

Gregory

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful
Stayed 2 nights in Sep 2024

6/10 Okay

Robert, Portland

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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

Travelled 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