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

    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $149 nightly
    The price is $166 total per night from Jul 5 to Jul 6
    $166 total
    Jul 5 - Jul 6
    Total with taxes and fees
    9/10 Wonderful! (962 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $145 nightly
    The price is $162 total per night from Jun 7 to Jun 8
    $162 total
    Jun 7 - Jun 8
    Total with taxes and fees
    8.8/10 Excellent! (2,389 reviews)
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $111 nightly
    The price is $124 total per night from Jun 7 to Jun 8
    $124 total
    Jun 7 - Jun 8
    Total with taxes and fees
    9.2/10 Wonderful! (1,003 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
345 Vacation Homes
Lowest Price
$124
Highest Price
$317
Popular accommodation
Cozy Riverside Berkshires Retreat, The Meadows House @ Otis Ridge w/ 7-person hot tub, The Great Escape Ski Cottage w/HOT TUB @ Great Barrington , Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Peace and quiet on the lake, Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay, Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!, Summer Chalet w/ Pool, Firepit + Private Hiking Trails in Great Barrington, Charming Berkshire Retreat-Minutes to Williamstown

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