The Berkshires 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 The Berkshires

Don't see what you're looking for?
See all available properties in The Berkshires
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 The Berkshires

    Hotel Downstreet, Ascend Hotel Collection

    Hotel Downstreet, Ascend Hotel Collection

    40 Main St, North Adams, MA
    $144 nightly
    The price is $160 total per night from Aug 3 to Aug 4
    $160 total
    Aug 3 - Aug 4
    Total includes taxes and fees
    8.6/10 Excellent! (1,004 reviews)
    Prospect Berkshires

    Prospect Berkshires

    50 Prospect Lake Rd, Egremont, MA
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Williamstown, MA
    $117 nightly
    The price is $131 total per night from Jul 5 to Jul 6
    $131 total
    Jul 5 - Jul 6
    Total includes taxes and fees
    8.6/10 Excellent! (1,845 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
356 Vacation Homes
Lowest Price
$131
Highest Price
$160
Popular accommodation
Deluxe Queen Room with 2 Queen Beds, Imagine Being Lakeside This Summer! Book Now!, 4 Mi to Great Barrington: Berkshires Retreat!, Stay Lakeside This Summer!, Lake Front Home in Heart of the Berkshires Near Jiminy Peak, Rustic 3bd Lake Front Country Cottage, Spectacular views and close to Great Barrington., Garfield Townhouse in the Berkshires on Main St, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!