Compare The Berkshires Cottage Rentals

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Featured Cottages 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
    $130 nightly
    The price is $145 total per night from May 31 to Jun 1
    $145 total
    May 31 - Jun 1
    Total with taxes and fees
    9/10 Wonderful! (955 reviews)
    Berkshires Untold

    Berkshires Untold

    194 Pittsfield Rd Lenox MA
    $119 nightly
    The price is $133 total per night from Jun 1 to Jun 2
    $133 total
    Jun 1 - Jun 2
    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
    $128 nightly
    The price is $143 total per night from May 31 to Jun 1
    $143 total
    May 31 - Jun 1
    Total with taxes and fees
    8.8/10 Excellent! (2,375 reviews)

Cottages

Book a cottage in The Berkshires
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in The Berkshires. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know The Berkshires better.

Cottage apartments in The Berkshires range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in The Berkshires
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in The Berkshires and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a The Berkshires cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in The Berkshires. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

The Berkshires Cottages essential information

Accommodation
85 Cottages
Lowest Price
$133
Highest Price
$145
Popular accommodation
The Blue Elm - A Historic Berkshire Cottage, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , 2-bedroom cottage close to hiking and swimming with AC, A-frame Cabin w/ Furnished Deck in Becket!, Private Island - Largest Fresh Water Reservoir in Mass, Private Lake Cottage on 3 acres w/350 sq. ft. deck , Waterfront Cottage 10 Min From Great Barrington, Charming historic cottage on scenic road to Mt. Greylock, LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE

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