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

    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 Aug 31 to Sep 1
    $143 total
    Aug 31 - Sep 1
    Total with taxes and fees
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $152 nightly
    The price is $170 total per night from Sep 27 to Sep 28
    $170 total
    Sep 27 - Sep 28
    Total with taxes and fees
    9.2/10 Wonderful! (1,022 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $125 nightly
    The price is $139 total per night from Aug 31 to Sep 1
    $139 total
    Aug 31 - Sep 1
    Total with taxes and fees
    9/10 Wonderful! (1,094 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
73 Cottages
Lowest Price
$139
Highest Price
$170
Popular accommodation
Charming historic cottage on scenic road to Mt. Greylock, Private Island - Largest Fresh Water Reservoir in Mass, Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Waterfront Cottage 10 Min From Great Barrington, A-frame Cabin w/ Furnished Deck in Becket!, The Blue Elm - A Historic Berkshire Cottage, Berkshire Hills Nature Lovers' Log Home Retreat, Berkshires Cabin 2 Mi to Appalachian Trail!

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