Waterfront vacation rentals in Berkshire County

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Berkshire County

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

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Guest favorite

Home in Becket

4.93 out of 5 average rating, 118 reviews

Lake front retreat - Stylish Berkshire home

Drive down a lovely country wooded road to this renovated 4 bedroom mid century home on Long Bow Lake. The house has wood floors throughout & hip design. Gas fireplace in the dining room. This will be a home for the family to enjoy. We have our own private lake frontage that includes a dock & 4 kayaks. Enjoy the screened in porch, Weber gas grill, ping pong table & games. The area is quiet & peaceful only 20 minutes from Downtown Lee, Outlets, fabulous hikes & minutes from skiing Otis Ridge.

Dec 14 – 21

G$72,080 GYD per night

Guest favorite

Apartment in Williamstown

4.96 out of 5 average rating, 299 reviews

New Studio In Town, By the Water

★ New to Williamstown? Explore our interactive guidebook. Charming studio just steps away from shops, restaurants & few minutes’ walk to Williams College. Renovated and well-equipped, this home offers a wonderful view of Water Street. If you like the outdoors, descend on the Green River back of the property. The wooded riverbank with Adirondack chairs, and picnic tables is great for relaxing while enjoying your evening sundowners by the fire pit with the sound of the river in the background.

May 22 – 29

G$31,722 GYD per night

Guest favorite

Home in Great Barrington

4.96 out of 5 average rating, 139 reviews

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.

Apr 18 – 25

G$89,544 GYD per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

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.

Mar 22 – 29

G$26,884 GYD per night

Guest favorite

Home in Huntington

4.9 out of 5 average rating, 109 reviews

Private house on the River

Get away from it all at this very private house on the Westfield River. Walk in and feel right at home in this comfortable 2 bedroom ranch. It has a large back porch with outdoor seating and table that is 50 steps from the river. We supply everything you need, from the sheets and towels to your basic cooking needs. All you need to do is the bring the food. This house is perfect for families, with a large yard, indoor and outdoor toys, tire swing, floats, pack & play and high chair.

Jan 26 – Feb 2

G$39,455 GYD per night

Superhost

Cottage in Canaan

4.9 out of 5 average rating, 126 reviews

Plan your Berkshires by the lake

Very comfortable three-bedroom cottage in a quiet, private association on Queechy Lake. There is also a pullout queen size couch. Perfect for families. Hi-speed Spectrum internet, AllClad cookware, electric range, microwave, sharp knives, coffee maker, charcoal BBQ, and tons of places to hike. Apple TV and a Bose Bluetooth soundbar. There is also a large Solo Stove firepit as well as 2 kayaks and a paddle board for tooling around the lake. Close to supermarkets. 15 minutes to Tanglewood!

Sep 9 – 16

G$54,842 GYD per night

Superhost

Cottage in Florida

4.82 out of 5 average rating, 101 reviews

Peaceful Mountain Cabin by Ski, Kayak, Museums +!

ENJOY A MOUNTAIN ADVENTURE You will fall in love with this magic cottage nestled within 2 acres of old growth forest. Breathe in the fresh air enjoying the mountain vistas and sipping some hot cocoa. Warm up by the pellet stove or gaze at the stars seating by the fire pit. Berkshire East Ski is a few min away as well as the famous hairpin turn and many national forests. MASS MoCA only 15 min away, and Mt. Greylock is nearby as well as many outdoor adventures, restaurants & pubs.

Nov 12 – 19

G$29,605 GYD per night

Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 128 reviews

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.

Aug 17 – 24

G$98,742 GYD per night

Guest favorite

Cabin in Lee

4.9 out of 5 average rating, 102 reviews

Spring sale! Cabin with views in the Berkshires

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!

Nov 19 – 26

G$80,291 GYD per night

Guest favorite

Home in New Marlborough

4.89 out of 5 average rating, 122 reviews

Lake House in the Berkshire (Access Dock & Canoe

Unwind and reset at a newly built house on Lake Buel. With access to a private community dock and provided canoe, you can take advantage of life on the water. Inside this newly built house, you will find brand new furnishings and newly updated features to make your stay comfortable. Just a quick five minute drive to Great Barrington, home to some of the best restaurants that the Berkshires have to offer.

Oct 2 – 9

G$67,401 GYD per night

Superhost

Cottage in Lanesborough

4.85 out of 5 average rating, 250 reviews

Wildlife Lakeside Cottage

Fully furnished , totally remodeled ( completed in Feb. 2016), private cottage set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. For conditions message Jill.

Feb 14 – 21

G$57,098 GYD per night

Guest favorite

Home in Sheffield

4.93 out of 5 average rating, 111 reviews

A Private Peninsula Retreat In The Berkshires!

THIS IS MY DREAM COME TRUE!!! I finally found the most perfect lake house in the Berkshires! It is a 2 acre private peninsula jutting out into Mill Pond! Come kayak, stand up paddle, canoe, fish on the pond & hang out on the dock and the deck! 3 bedrooms & 2 full baths- can sleep up to 12. Enjoy music, theater, dance, hiking, museums, skiing, dining, relaxing in the Berkshires!

Apr 25 – May 2

G$85,622 GYD per night