Cheshire Vacation Homes

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Hotel Options in Cheshire

    Harbour House Inn

    Harbour House Inn

    725 North State Road Cheshire MA
    $249 nightly
    The price is $264 total per night from Dec 1 to Dec 2
    $264 total
    Dec 1 - Dec 2
    Total with taxes and fees
    9.6/10 Exceptional! (38 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $94 nightly
    The price is $105 total per night from Nov 23 to Nov 24
    $105 total
    Nov 23 - Nov 24
    Total with taxes and fees
    8.6/10 Excellent! (2,136 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $120 nightly
    The price is $135 total per night from Nov 30 to Dec 1
    $135 total
    Nov 30 - Dec 1
    Total with taxes and fees
    9/10 Wonderful! (755 reviews)

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
Vacation Homes
Lowest Price
$105
Highest Price
$264
Popular accommodation
Harbour House Inn, Vacation Village in the Berkshires, Berkshire Mountain Lodge