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Winchester Inn

Property class: 3.5

Photo gallery for Winchester Inn

Front of property
Bar (on property)
Suite, 2 Bedrooms (Duet Suite) | Living area
Suite, 1 King Bed (Hargadine) | Living room
Suite, 1 King Bed (Hargadine)

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free Wi-Fi
  • Air-conditioning
  • Business services
The current price is NZ$541
includes taxes & fees
30 Apr - 1 May

Explore the area

View map
35 S. 2nd St., Ashland, OR, 97520
  • Place, Oregon Cabaret Theatre
    ‪1 min walk‬
  • Place, Oregon Shakespeare Festival
    ‪3 min walk‬
  • Place, Allen Elizabethan Theatre
    ‪5 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)

Double Room, 1 Bedroom (Garden)

10.0 out of 10
Exceptional
(1 review)
  • 33 sq m
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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

Double Room, 1 Bedroom (Sylvan)

Double Room, 1 Bedroom (Sylvan)

9.6 out of 10
Exceptional
(5 reviews)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed

View all photos for Double Room (Queen Anne)

Double Room (Queen Anne)

Double Room (Queen Anne)

10.0 out of 10
Exceptional
(1 review)
  • 33 sq m
  • Sleeps 2
  • 1 Queen Bed and 1 Single Bed

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

Double Room, 1 Queen Bed (Patio)

Double Room, 1 Queen Bed (Patio)

9.4 out of 10
Exceptional
(3 reviews)
  • 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)

  • 33 sq m
  • Sleeps 2
  • 1 Queen 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)

10.0 out of 10
Exceptional
(5 reviews)
  • 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)

10.0 out of 10
Exceptional
(2 reviews)
  • 37 sq m
  • Sleeps 2
  • 1 King 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)

10.0 out of 10
Exceptional
(3 reviews)
  • 37 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)

  • 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)

10.0 out of 10
Exceptional
(1 review)
  • 33 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)

10.0 out of 10
Exceptional
(1 review)
  • 37 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)

7.0 out of 10
Good
(2 reviews)
  • 46 sq m
  • 1 bedroom
  • 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)

  • 65 sq m
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed

View all photos for Suite, 1 King Bed (Hargadine)

Suite, 1 King Bed (Hargadine)

Suite, 1 King Bed (Hargadine)

  • 84 sq m
  • 1 bedroom
  • 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)

  • 46 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)

9.0 out of 10
Wonderful
(2 reviews)
  • 46 sq m
  • Sleeps 2
  • 1 King Bed

View all photos for Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

Suite, 1 Bedroom (Silverdale)

8.0 out of 10
Very good
(1 review)
  • 42 sq m
  • 1 bedroom
  • 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)

  • 42 sq m
  • 1 bedroom
  • Sleeps 2
  • 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)

  • 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)

10.0 out of 10
Exceptional
(1 review)
  • 42 sq m
  • Sleeps 2
  • 1 King Bed

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 - 1 min walk - 0.0 km
  • Oregon Shakespeare Festival - 3 min walk - 0.3 km
  • Lithia Park - 3 min walk - 0.3 km
  • Allen Elizabethan Theatre - 5 min walk - 0.4 km
  • Angus Bowmer Theatre - 5 min walk - 0.4 km

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 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
  • ‪Mezcal - ‬6 min walk

About this property

Winchester Inn

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.

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Ashland Springs Hotel
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  • Spa
  • Pet-friendly
  • Parking included
  • Free Wi-Fi
4.6 out of 5, Wonderful, 1,004 reviews
The price is NZ$208
includes taxes & fees
27 Apr - 28 Apr
Ashland Springs Hotel

Property amenities

Internet

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

Parking and transport

  • Free self parking on site
  • Limited on-site self parking

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)

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

  • 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
Information provided by the property may be translated using automated translation tools

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:

  • A tax is imposed by the city: USD 9
  • 3 per cent 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
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that 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 and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts Visa, Mastercard, American Express and Discover. Cash is not accepted. For guests' safety, the property includes a fire extinguisher in all accommodation.

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 25 Apr 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on 30 Apr 2026 start from NZ$541, 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. 234 out of 272 reviews
Rating 8 - Good. 28 out of 272 reviews
Rating 6 - Okay. 4 out of 272 reviews
Rating 4 - Poor. 3 out of 272 reviews
Rating 2 - Terrible. 3 out of 272 reviews

9.8/10

Cleanliness

9.8/10

Staff & service

9.4/10

Amenities

9.6/10

Property conditions & facilities

Reviews

10/10 Excellent

Stacey

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

2/10 Terrible

Mei, Sunnyvale

Travelled with group
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

8/10 Good

James

Travelled with partner
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

10/10 Excellent

Jill

Stayed 1 night in Nov 2025

10/10 Excellent

Jack

Stayed 1 night in Dec 2025

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

10/10 Excellent

Ann

Stayed 1 night in Nov 2025

10/10 Excellent

Marcia

Stayed 1 night in Nov 2025

10/10 Excellent

JOHN AND NANCY

Stayed 1 night in Dec 2025

10/10 Excellent

Marcia

Stayed 1 night in Nov 2025

10/10 Excellent

Gloria

Stayed 1 night in Nov 2025

10/10 Excellent

David

Stayed 1 night in Nov 2025

6/10 Okay

Richard

Stayed 1 night in Oct 2025

10/10 Excellent

Carolyn

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

10/10 Excellent

Robert

Stayed 1 night in Sep 2025

10/10 Excellent

Patricia

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

10/10 Excellent

Joe

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

10/10 Excellent

Laura

Travelled with partner
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

10/10 Excellent

Shanna

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful property. The room was spacious and clean. The sheets were soft and the bed was comfortable. The wait staff was very professional and attentive. The breakfast was delicious and included in the stay. It was walkable to Old Town Ashland. We stayed on foot for most of our stay. Very close to Lithia Park, dining and entertainment. Highly recommend.
Stayed 2 nights in Sep 2025

10/10 Excellent

Christi

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

10/10 Excellent

Bette, Eugene

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful setting with great service and food. Only problem was the bees nest above our patio room. Couldn’t sit outside because of the bees.
Stayed 2 nights in Aug 2025

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

10/10 Excellent

Heather

Weekend getaway

The room was amazing, and perfect location . The only negative was how small the tv was but we didn’t end up using it do wasn’t a big deal. The fire place motor sounded like it was on when everything was turned off. The room was amazing and definitely will come back, breakfast was good only bummer was the expresso machine was broken. The bed was comfortable, and staff was great. I love the little touch and personalization in the room.
Stayed 1 night in Jul 2025

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

8/10 Good

Sid

Travelled with family
Liked: Cleanliness
The 2 full bedrooms with 2 large bathrooms was very convenient. Basically the unit is a converted garage surrounded by parking lots which made it noisy. Location is centrally located and excellent.
Stayed 2 nights in Jun 2025