Cheshire Vacation Homes

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Cheshire

Don't see what you're looking for?
See all available properties in Cheshire
View all properties
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
    $108 nightly
    The price is $121 total per night from Nov 17 to Nov 18
    $121 total
    Nov 17 - Nov 18
    Total with taxes and fees
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $106 nightly
    The price is $118 total per night from Dec 14 to Dec 15
    $118 total
    Dec 14 - Dec 15
    Total with taxes and fees
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $126 nightly
    The price is $141 total per night from Dec 12 to Dec 13
    $141 total
    Dec 12 - Dec 13
    Total with taxes and fees

Cheshire Vacation Homes

Book vacation homes in Cheshire
Next time you take a group getaway top Cheshire, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Cheshire vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Cheshire vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Cheshire; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Cheshire rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Cheshire is sure to be a winner.

Cheshire Vacation Homes essential information

Accommodation
260 Vacation Homes
Lowest Price
$118
Highest Price
$395
Popular accommodation
Experience Three Sisters Sanctuary in Goshen, MA, Cozy private 2 bed apartment in Shelburne Falls, Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room, Contemporary Berkshire Home with Views of Taconic Golf Course, Leaves are turning and wish you were watching! Warm days, cool nights weather., RENOVATED JIMINY PEAK MOUNTAINSIDE CONDO Designer Interiors • Walk to Slopes, Berkshire Lake access, Modern Designer Chalet on 5.5 Private Acres Near Tanglewood, stylish Berkshires Retreat