The Berkshires Vacation Homes

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Featured Vacation Homes in The Berkshires

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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 The Berkshires

    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $112 nightly
    The price is $125 total per night from Nov 2 to Nov 3
    $125 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.6/10 Excellent! (2,028 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr, Pittsfield, MA
    $113 nightly
    The price is $126 total per night from Nov 2 to Nov 3
    $126 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (668 reviews)
    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

    190 Meadow Street, South Lee, MA
    $129 nightly
    The price is $144 total per night from Nov 2 to Nov 3
    $144 total
    Nov 2 - Nov 3
    Total with taxes and fees
    9/10 Wonderful! (741 reviews)

The Berkshires Vacation Homes

Book vacation homes in The Berkshires
Next time you take a group getaway top The Berkshires, 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 The Berkshires vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every The Berkshires 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 The Berkshires; 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 The Berkshires 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 The Berkshires is sure to be a winner.

The Berkshires Vacation Homes essential information

Accommodation
360 Vacation Homes
Lowest Price
$125
Highest Price
$821
Popular accommodation
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Stockbridge Village in Summer, NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE, Spacious 5-bedroom house in charming Lee with WiFi, Amore Estate - beautiful room with many places to explore and relax in., Contemporary Berkshire Home with Views of Taconic Golf Course, Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location, General Williams Estate House Lenox/Stockbridge, Cheerful 3-bedroom cottage with woodstove

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