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Waterfront vacation rentals in Berkshire County

Find and book unique waterfront rentals on Airbnb

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Top-rated waterfront rentals in Berkshire County

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in Great Barrington
Elegant Year-Round Lakeside Retreat with AC
The Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Newly installed mini-splits provide AC in all bedrooms and LVR/DR/Kitchen common area. 1 house-trained dog ok.
Oct 11 – 18
$399 per night
Guest favorite
Guest suite in South Lee
Sunny Riverside Apartment
The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.
Dec 2 – 9
$112 per night
Guest favorite
Cottage in Becket
Cozy lakeside cottage
Two-bedroom cottage on the lake with a dock nestled in the woodsy Sherwood Forest Community. Relax with the whole family at our quiet and peaceful oasis. You can swim, fish, kayak, and canoe in the water right from our private beach. Great place for a lakeside campfire at night. Our dock is perfectly situated for practicing yoga, meditation or quiet contemplation. Please note that accessing the house as well as getting down to the dock requires climbing stairs.
Nov 7 – 14
$234 per night

Popular amenities for Berkshire County waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Williamstown
New Studio In Town, By the Water
Mar 9 – 16
$122 per night
Superhost
Apartment in Williamstown
Williamstown Apt. on Green River Walk to Williams!
Mar 3 – 10
$147 per night
Guest favorite
Apartment in Canaan
Queechy Lake Carriage House
Oct 20 – 27
$81 per night
Guest favorite
Apartment in Lanesborough
Cozy Berkshire Waterfront Home
Mar 29 – Apr 5
$138 per night
Superhost
Apartment in Great Barrington
Zen River Studio
Mar 28 – Apr 4
$173 per night
Guest favorite
Apartment in Otis
Enjoy every season the Berkshires have to offer.
Mar 14 – 21
$135 per night
Apartment in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
Jun 29 – Jul 6
$298 per night
Guest favorite
Apartment in Great Barrington
2 bdrm.Riverhouse in the Berkshires
Aug 28 – Sep 4
$189 per night
Guest favorite
Apartment in Pittsfield
The sweet place in the beautiful Berkshires!
Feb 15 – 22
$105 per night
Guest favorite
Apartment in Pittsfield
Luxury 2BR Apt. Home w/Work Area
Aug 8 – 15
$110 per night
Guest favorite
Apartment in Stockbridge
Three bedroom duplex in Stockbridge on the river
Apr 28 – May 5
$203 per night
Guest favorite
Apartment in Adams
Lovely Guesthouse with office. In Berkshires
Jun 18 – 25
$95 per night

Waterfront house rentals

Guest favorite
Home in Becket
Lake front retreat - Stylish Berkshire home
Jun 23 – 30
$499 per night
Guest favorite
Home in Otis
Idyllic family retreat - spacious lake home,
Mar 25 – Apr 1
$210 per night
Guest favorite
Home in Huntington
Private house on the River
Apr 29 – May 6
$165 per night
Guest favorite
Home in Sheffield
A Private Peninsula Retreat In The Berkshires!
May 19 – 26
$411 per night
Guest favorite
Home in New Marlborough
Lake House in the Berkshire (4min to Ski ButterNut
Aug 9 – 16
$331 per night
Guest favorite
Home in Austerlitz
Peaceful Renovated Barn in the Berkshires
May 9 – 16
$273 per night
Guest favorite
Home in Becket
Lindal Cedar Berkshires Lake House
Dec 13 – 20
$385 per night
Guest favorite
Home in Great Barrington
Waterfront Modern Lake Mansfield Retreat
Jun 11 – 18
$713 per night
Guest favorite
Home in Becket
Secluded lakeside charmer
May 13 – 20
$213 per night
Guest favorite
Home in Canaan
Private Retreat! Hot Tub, Pool Table & Movie Room
Apr 3 – 10
$254 per night
Guest favorite
Home in Becket
Lakefront Cottage on Private Beach
Sep 20 – 27
$231 per night
Home in Becket
New Shaw Pond Skytop Retreat in the Berkshires
Oct 30 – Nov 6
$261 per night

Destinations to explore