Cheshire Vacation Homes

Featured Vacation Homes in Cheshire

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

$743 nightly
The price is $830 total per night
$830 total
Jul 30 - Jul 31
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Washer
Dryer
Charming Berkshires Retreat – Minutes to Williamstown

Charming Berkshires Retreat – Minutes to Williamstown

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
Kitchen
Washer
Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

At this vacation home, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free vacation home also has barbecue grills.
Pool
Kitchen
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

At this vacation home, guests have access to a garden.
Air conditioning
Outdoor Space
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
19th c. Barn in the Berkshires

19th c. Barn in the Berkshires

At this vacation home, guests have access to a library, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Kitchen
Washer
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

This vacation home features a hot tub and a garden.
Hot Tub
Kitchen
Art House! Spacious Getaway By Mass Moca

Art House! Spacious Getaway By Mass Moca

Guests staying at this vacation home enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free vacation home also has a garden.
Hot Tub
Kitchen
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Cheshire

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $110 nightly
    The price is $123 total per night from Jul 20 to Jul 21
    $123 total
    Jul 20 - Jul 21
    Total includes taxes and fees
    8.6/10 Excellent! (1,877 reviews)
    The Williams Inn

    The Williams Inn

    101 Spring Street, Williamstown, MA
    $269 nightly
    The price is $301 total per night from Aug 10 to Aug 11
    $301 total
    Aug 10 - Aug 11
    Total includes taxes and fees
    9.6/10 Exceptional! (468 reviews)
    Hotel Downstreet, Ascend Hotel Collection

    Hotel Downstreet, Ascend Hotel Collection

    40 Main St, North Adams, MA
    $161 nightly
    The price is $179 total per night from Aug 17 to Aug 18
    $179 total
    Aug 17 - Aug 18
    Total includes taxes and fees
    8.6/10 Excellent! (999 reviews)

Vacation Homes in Cheshire

More Places To Stay in Cheshire