Compare The Berkshires Cottage Rentals

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 Cottages 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

    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 Nov 1 to Nov 2
    $143 total
    Nov 1 - Nov 2
    Total with taxes and fees
    8.8/10 Excellent! (2,735 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $115 nightly
    The price is $128 total per night from Nov 10 to Nov 11
    $128 total
    Nov 10 - Nov 11
    Total with taxes and fees
    9/10 Wonderful! (1,200 reviews)
    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $106 nightly
    The price is $118 total per night from Nov 1 to Nov 2
    $118 total
    Nov 1 - Nov 2
    Total with taxes and fees

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
$118
Highest Price
$571
Popular accommodation
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , Private Island - Largest Fresh Water Reservoir in Mass, Cozy Cottage-Sunset On The Lake , LAKE GARFIELD WATERFRONT HOME AND BOATHOUSE, Charming historic cottage on scenic road to Mt. Greylock, The Blue Elm - A Historic Berkshire Cottage, Waterfront Cottage 10 Min From Great Barrington, 2-bedroom cottage close to hiking and swimming with AC

More to Explore