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

    Hotel Downstreet, an Ascend Collection Hotel

    Hotel Downstreet, an Ascend Collection Hotel

    40 Main St North Adams MA
    $170 nightly
    The price is $190 total per night from Jun 30 to Jul 1
    $190 total
    Jun 30 - Jul 1
    Total with taxes and fees
    8.8/10 Excellent! (1,013 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $155 nightly
    The price is $173 total per night from Jun 15 to Jun 16
    $173 total
    Jun 15 - Jun 16
    Total with taxes and fees
    9/10 Wonderful! (978 reviews)
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd Williamstown MA
    $136 nightly
    The price is $152 total per night from Jun 15 to Jun 16
    $152 total
    Jun 15 - Jun 16
    Total with taxes and fees
    8.8/10 Excellent! (2,394 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
$152
Highest Price
$376
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 , Spacious Living, Covered Porch & Forest Setting | Beaver Creek by AvantStay, Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets. , Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!, Imagine Being Lakeside, Kayaks/Fishing/EV Charger, Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!, Great Barrington, Cabin Sleeps 14, Walk To Town

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