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Winchester Inn

Property class: 3.5

Choose dates to view prices

Close to Oregon Shakespeare Festival, Winchester Inn provides free cooked-to-order breakfast, a terrace and a garden. Stay connected with free in-room WiFi, and guests can find other amenities, such as dry cleaning/laundry services and a bar.

Reviews

9.6 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free Wi-Fi
  • Air-conditioning
  • Business services
The current price is ₹17,199
₹20,901 total
includes taxes & fees
31 Aug - 1 Sept

Room options

Available filters for rooms
Showing 23 of 23 rooms

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

A bedroom with a large bed, a sofa, a small table, and a dresser. There is a window with curtains and a view of greenery outside.

Double Room, 1 Bedroom (Garden)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

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

A bedroom with a bed, bedside lamps, a window with curtains, a sofa, a small table, and a bathroom with a sink and mirror.

Double Room, 1 Bedroom (Sylvan)

9.8 out of 10
Exceptional
(6 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Double Room (Queen Anne)

A hotel room with a large bed, two armchairs, a small table, a TV, and a mirror.

Double Room (Queen Anne)

10.0 out of 10
Exceptional
(1 review)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Single Bed
  • Free Wi-Fi

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

A bedroom with a large bed, a chair, a desk, and a window with curtains.

Double Room, 1 Queen Bed (Patio)

9.4 out of 10
Exceptional
(3 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

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

A bedroom with a bed, a desk, a chair, and a television.

Double Room, 1 Queen Bed (Marjorie Roy)

  • 350 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

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

A bedroom with a large bed, a bedside table with a lamp, a wardrobe, and a window with curtains.

Double Room, 1 Queen Bed (Catharine M)

10.0 out of 10
Exceptional
(5 reviews)
  • 300 sq ft
  • Sleeps 2
  • 1 Queen Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Sunset)

A spacious bedroom with a large bed, bedside lamps, a wooden headboard, and a piano in the corner.

Double Room, 1 King Bed (Sunset)

9.4 out of 10
Exceptional
(3 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Andrew G)

A cozy living room with a beige sofa, a patterned armchair, a small table with a lamp, and a window with curtains.

Double Room, 1 King Bed (Andrew G)

10.0 out of 10
Exceptional
(3 reviews)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Peter Benjamin)

A bedroom with a large bed, a wooden wardrobe, a sofa, and a small table.

Double Room, 1 King Bed (Peter Benjamin)

  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Eastlake)

A well-lit room with a large mirror, a wooden cabinet, a floral armchair, a beige sofa, and a bed with a quilted cover.

Double Room, 1 King Bed (Eastlake)

10.0 out of 10
Exceptional
(2 reviews)
  • 350 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Double Room, 1 King Bed (Enders)

A hotel room with a bed, a sofa, a desk with a coffee maker, and a TV on the wall.

Double Room, 1 King Bed (Enders)

10.0 out of 10
Exceptional
(1 review)
  • 400 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed with Sofa bed (Robert Gordon)

A bedroom with a large bed, wooden furniture, and a view of the outdoors.

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

7.0 out of 10
Good
(2 reviews)
  • 500 sq ft
  • 1 bedroom
  • Sleeps 4
  • 1 King Bed and 1 Single Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 2 Bedrooms (Duet Suite)

A bedroom with a large bed, bedside lamps, a nightstand, a window with curtains, and a ceiling light.

Suite, 2 Bedrooms (Duet Suite)

  • 700 sq ft
  • Sleeps 4
  • 1 King Bed, 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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

A bedroom with a bed, dresser, chair, and a television on the wall.

Suite, 1 King Bed (Hargadine)

  • 900 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Barbara Howard)

A four-poster bed with a canopy, a bedside table with a lamp, a dresser with mirrors, and a view of the outdoors through a window.

Suite, 1 King Bed (Barbara Howard)

  • 500 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 King Bed (Eleanor Rose)

A bedroom with a high, sloped ceiling, a large bed, two bedside tables, a chair, and a window.

Suite, 1 King Bed (Eleanor Rose)

9.0 out of 10
Wonderful
(2 reviews)
  • 500 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, 1 Bedroom (Silverdale)

A bedroom with a wooden ceiling, a bed with floral bedding, a chair, a desk, and a framed picture on the wall.

Suite, 1 Bedroom (Silverdale)

8.0 out of 10
Very good
(1 review)
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Single Murphy Bed
  • Free Wi-Fi

View all photos for Suite, 1 Queen Bed with Sofa bed (Brighton)

A neatly arranged bedroom with a large bed, two bedside tables, a dresser, and a window with curtains.

Suite, 1 Queen Bed with Sofa bed (Brighton)

  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Suite, 1 Queen Bed with Sofa bed (Courtyard)

A bedroom with a bed, bedside table, lamp, and a window with blinds.

Suite, 1 Queen Bed with Sofa bed (Courtyard)

  • 450 sq ft
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

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

A bedroom with a large bed, two bedside lamps, a fireplace, and a view of the outdoors.

Suite, 1 King Bed (Fordyce)

10.0 out of 10
Exceptional
(1 review)
  • 450 sq ft
  • Sleeps 2
  • 1 King Bed
  • Free Wi-Fi

View all photos for Suite, Garden View

A bedroom with a bed, a grey sofa, a white armchair, a small table, and a fireplace.

Suite, Garden View

  • Garden view
  • 450 sq ft
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed and 1 Double Sofa Bed
  • Free Wi-Fi

View all photos for Family Suite, City View

A modern living room with a sofa, coffee table, and a TV. There is a large window with curtains, a mirror, and a view of a bedroom.

Family Suite, City View

  • City view
  • 850 sq ft
  • 2 bedrooms
  • Sleeps 5
  • 1 King Bed, 1 Queen Bed and 1 Single Bed
  • Free Wi-Fi

View all photos for Superior Suite, Mountain View

A hotel room with a bed, a chair, a sofa, a TV, and a lamp.

Superior Suite, Mountain View

  • Mountain view
  • 500 sq ft
  • 1 bedroom
  • Sleeps 3
  • 1 King Bed and 1 Double Sofa Bed
  • Free Wi-Fi
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About the area

Located in Historic Downtown District, a neighbourhood in Ashland, Winchester Inn is in a shopping district. Weisinger Family Winery and Grizzly Peak Winery are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore North Mountain Park and Cascade-Siskiyou National Monument. ScienceWorks Hands-On Museum and The RRRink are also worth visiting. Visit our Ashland travel guide
View more Inns in Ashland
Map
35 S. 2nd St., Ashland, OR, 97520

What's nearby

  • A statue of a person in a brown outfit with a hat and sunglasses, holding a pipe and a book, standing on a pedestal in a park with green bushes and trees.
    Oregon Shakespeare Festival
    3 min walk - 0.3 km
  • A pond with ducks, surrounded by trees and a small bridge.
    Lithia Park
    3 min walk - 0.3 km
  • Oregon Cabaret Theatre
    1 min walk - 0.1 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

  • Arbor House
    11 min drive
  • Ceremony
    11 min drive
  • Xerxes Mediterranean Grill
    5 min drive
  • Wendy's
    4 min drive
  • Wild Goose Cafe & Bar
    6 min drive

About this property

Winchester Inn

  • Inn near Oregon Shakespeare Festival
  • You can look forward to free cooked-to-order breakfast, a terrace and a garden at Winchester Inn. Free in-room WiFi is available to all guests, along with dry cleaning/laundry services and a bar.
  • You'll also find perks such as:
    • Free self-parking
    • Smoke-free property, a gift shop and concierge services
    • Free newspapers, luggage storage and tour/ticket information
    • Guest reviews speak highly of the helpful staff
  • Room features
  • All guest rooms are individually furnished, and include comforts, such as premium bedding and laptop-friendly workspaces, in addition to thoughtful touches, such as air conditioning and bathrobes.
  • More conveniences in all rooms include:
    • Hypo-allergenic bedding, Egyptian cotton sheets and pillowtop mattresses
    • Designer toiletries and hairdryers
    • Flat-screen TVs with cable channels
    • Wardrobes/cupboards, electric kettles and heating

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₹12,000 total
includes taxes & fees
1 Sept - 2 Sept
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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

  • Hardwood flooring in room
  • High-pile carpet in room
  • No lift

More

  • 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

  • Designer toiletries
  • Dressing gowns
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Flat-screen TV with cable channels

Food and drink

  • Coffee/tea maker
  • Electric kettle
  • Minibar

More

  • Air conditioning
  • Connecting rooms available
  • Heating
  • Individual decor
  • Individual furnishings
  • Iron/ironing board
  • Laptop workspace
  • 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

Pets not allowed

Children and extra beds

Children are welcome
Cots (infant beds) are not available

Payment types at the property

Important information

Fees

You'll be asked to pay the following charges at the property. Fees may include applicable taxes:

  • A tax is imposed by the city: USD 9
  • 4 per cent destination fee will be charged.
  • Administrative fee: USD 10.00 per accommodation, per night

We have included all charges provided to us by the property.

Optional extras

  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may 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
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

We should mention

This property does not have any lifts
Only registered guests are allowed in the guestrooms
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation

Frequently asked questions

Is Winchester Inn pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Winchester Inn?

As of 24 Aug 2026, prices found for a 1-night stay for 2 adults at Winchester Inn on 31 Aug 2026 start from ₹17,199, 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.

How much is parking at Winchester Inn?

Self-parking is free at this property.

What time is check-in at Winchester Inn?

Check-in start time: 4:00 PM; check-in end time: 9 PM. Late check-in is available during limited hours.

What time is check-out at Winchester Inn?

Checkout is at 11 AM. Late checkout is available for a fee.

Where is Winchester Inn located?

Located in Historic Downtown District, this inn is within a 5-minute walk of Oregon Cabaret Theatre and Oregon Shakespeare Festival. Ashland Library and Lithia Park are also within 5 minutes.

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