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Winchester Inn

3.5 star property
Comfortable Victorian inn, walk to Oregon Shakespeare Festival

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Photo gallery for Winchester Inn

Front of property
Double Room, 1 Queen Bed (Patio) | Terrace/patio
Double Room, 1 King Bed (Enders)
Suite, 1 Queen Bed with Sofa bed (Courtyard)
Double Room, 1 King Bed (Eastlake)
Reviews
9.8

Exceptional

Popular amenities

  • Breakfast included
  • Parking includedParking includedParking included
  • Free WiFiFree WiFiFree WiFi
  • HousekeepingHousekeepingHousekeeping
  • Restaurant
  • BarBarBar

Explore the area

Map
35 S. 2nd St., Ashland, OR, 97520
  • Popular LocationLithia Park4 min walk
  • Popular LocationOregon Shakespeare Festival4 min walk
  • Popular LocationSouthern Oregon University16 min walk
  • AirportMedford, OR (MFR-Rogue Valley Intl.)21 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)

10/10 Exceptional

Highlights

Furnished 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)

10/10 Exceptional

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
  • 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)

10/10 Exceptional

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

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
Pillow-top bed
  • 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)

10/10 Exceptional

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)

10/10 Exceptional

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
  • 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
Pillow-top bed
  • 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)

10/10 Exceptional

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)

10/10 Exceptional

Highlights

Individually furnished
Individually decorated
Air conditioning
Heating
Free rollaway/extra beds
Flat-screen TV
Hypo-allergenic bedding
Pillow-top bed
  • 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)

10/10 Exceptional

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)

10/10 Exceptional

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)

10/10 Exceptional

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

Front of property
The Bard's Inn, BW Signature Collection by Best Western
Pool
Breakfast included
Pet-friendly
Parking included
4.4 out of 5, Excellent, (1001)
The price is AU$504
for 1 night
includes taxes & fees
14 June - 15 June
The Bard's Inn, BW Signature Collection by Best Western

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 Oregon Shakespeare Festival. 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 Ashland Library and Lithia Park.
View more Inns in AshlandOpens in a new window

What's nearby

  • Oregon Cabaret Theatre - 2 min walk
  • Lithia Park - 4 min walk
  • Oregon Shakespeare Festival - 4 min walk
  • Allen Elizabethan Theatre - 5 min walk
  • Southern Oregon University - 16 min walk

Getting around

  • Medford, OR (MFR-Rogue Valley Intl.) - 22 min drive

Restaurants

  • Skout Taphouse & Provisions - 6 min walk
  • Gil's - 6 min walk
  • The Growler Guys - 3 min walk
  • Martolli's Hand Tossed Pizza - 5 min walk
  • Brickroom - 6 min walk

About this property

Winchester Inn

Comfortable Victorian inn, walk to 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 duvets and premium bedding. Flat-screen televisions come with cable channels.

Bathrooms include dressing gowns, 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
  • Daily housekeeping
  • Dry cleaning/laundry service
  • 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

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 staff will greet guests on arrival

Access methods

Staffed front desk

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
  • 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 31 May 2024, prices found for a 1-night stay for 2 adults at Winchester Inn on 2 June 2024 start from AU$290.75, 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?

You bet, guests adore the free cooked-to-order brekkie here! Offered daily between 8 AM and 9:30 AM, this is the perfect spot to fuel up for a day full of adventure.

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

9.8

Exceptional

Rating 10 - Excellent. 175 out of 203 reviews" "
Rating 8 - Good. 23 out of 203 reviews" "
Rating 6 - Okay. 1 out of 203 reviews" "
Rating 4 - Poor. 2 out of 203 reviews" "
Rating 2 - Terrible. 2 out of 203 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

Hong

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The room looks very nice. The hotel is in downtown, within walking distance to a few dinning options. It is very continent. The staff is nice. We’d love to stay again!
Stayed 1 night in Jan 2024

10/10 Excellent

Sarah

Stayed 1 night in Jan 2024

10/10 Excellent

carolyn

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Wonderful
Amazing room with a balcony, fire place, comfy bed and beautiful walk in shower. It was so nice having a beautiful restaurant down stairs.
Cozy and able to stream to the TV
So comfortable
Stayed 1 night in Dec 2023

10/10 Excellent

Ellen

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

10/10 Excellent

Kari

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Amazing!!
I came here on a solo vacation and everyone was absolutely amazing the entire time I was there! The inn itself was absolutely beautiful and the food was so delicious!! I will definitely be back!!
Stayed 2 nights in Nov 2023

10/10 Excellent

Anita

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

10/10 Excellent

Enrique Emanuel

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Located very close to downtown Ashland. Comfortableand clean rooms. All instructions for guests are clearly provided in a series of messages throughout the room and bathroom. The staff is very friendly, and the breakfast is plentiful, varied, and delicious. Choose it if you would like to know the city on foot.
Stayed 1 night in Oct 2023

10/10 Excellent

Margaux

Business traveller
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 3 nights in Oct 2023

10/10 Excellent

Amos

Travelled with partner
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The thing that won me over the most was their attention to detail. While the property wasn’t overly “luxurious”, the personal touches made us feel special. We would love to stay here again in the future!
Stayed 2 nights in Oct 2023

10/10 Excellent

Mary

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