
Waterfront vacation rentals in Great Barrington
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Top-rated waterfront rentals in Great Barrington
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

The Red Cabin-Secluded Getaway with backyard Brook
Welcome to our secluded mid-century cabin nestled in the foothills of the Berkshires in Northwestern CT! When you stay here you'll find over three private acres of ferns, forests, wild flowers and a native trout brook a stone's throw from the backdoor with your private hot tub to relax in. Beyond the brook are hundreds of acres of state forest preserve. Enjoy great hiking, fishing, skiing, antiques and restaurants minutes away. Only 2 hours from NYC and 8 minutes to Historic Norfolk Center.

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.

King Bed, Wi-Fi, 2m Ski Resort
Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. * 1.5 miles to Downtown * 1.3 miles to Mahaiwe Performing Arts Center * 44 miles to Albany International Airport *4.5 miles to Great Barrington Airport KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *55" Youtube TV with NFL Pack

Modern Mid-Century Cottage - Hike, Swim & Shop!
Let all your worries fade away in this beautifully remodeled modern cottage! Our 3 bedroom, 2 bath can sleep 8 adults in 2 Queen Beds, 2 Twin Beds and a Queen Sleeper Sofa. Relax by the fire pit out back or take out our 2 two person Kayaks and enjoy the lake in the summer, visit Catamount Ski Resort or other nearby ski mountains in the winter. The large, custom dinner table seats 8 comfortably with lots of room to hang, play games, watch movies and more. Guests must be 25 years old to rent.

Lake front retreat - Stylish Berkshire home
Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

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.

Rustic Pond Cabin: Nature, Stars & Serenity
Serene rustic cabin in Colebrook, Ct in beautiful Litchfield County! Cozy King bed under skylight, queen downstairs, woodstove and all the comforts of home. Pure clean pond- swim, fish, canoe n kayak! Sits far from main roads on quiet back road. Can walk, run or bike to local trails or stay and walk the trail around the pond, have campfires outside in firepit! Cleaned by me, no crazy rules n and surrounded by nature! Private Great WIFI! Close to quaint ski resorts n dispensaries

Carriage House on Falls, Walk to Village
Welcome to 1903 Carriage House on the Falls — just down the hill from the vibrant village of Saugerties. This cottage blends modern comfort with rustic charm. Its cozy size makes it the ultimate escape for couples seeking a tranquil getaway. Admire panoramic creek vistas from the back deck. Enjoy the outdoors with a gas grill and waterside gazebo, unwind with board games, or relax with a movie on the SmartTV. As night falls, drift off to the soothing sound of the waterfall.

Riverfront, Fireplace & Fire Pit -20 min to Hudson
Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Idyllic family retreat - spacious lake home,
This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

Captain's Quarters at Mickey's Marina
The Captain's Quarters is a one-of-a-kind rental experience at Copake Lake. Our 3-bedroom, 2-bathroom apartment features high ceilings and spacious living areas with a fresh take on the lake house aesthetic. Enjoy our open kitchen, living and dining area thoughtfully appointed with an island bar, large table and comfortable seating area. In the morning, sip your coffee or tea out on the front porch as you take in the lakeside views!

Design Lover’s Blue Cabin
Blue Cabin is a cozy, design-forward retreat between the Capital Region and the Berkshires. Enjoy vaulted wood ceilings, a forest-green kitchen, and a spa-style bath. Outside, unwind in the covered lounge with U-shaped sectional, charcoal grill, and TV—or explore the backyard, where a creek runs through and a seasonal flower garden blooms. Peaceful, private, and perfectly located for both rest and adventure.
Popular amenities for Great Barrington waterfront rentals
Waterfront apartment rentals

Suite 23 - Spacious Sunny 2-BR with Mountain view

Holland House: Modern Rustic Guest Apartment

Hudson River Beach House

Enjoy every season the Berkshires have to offer.

Majestic Farmhouse Private & Peaceful Guest Apt.

DeMew Townhouse in Historic Kingston

Scenic Hudson River Getaway!

Cozy 1 bedroom apartment in the Rondout Kingston
Waterfront house rentals

Everything on one floor 2 Bdrm/1.5 Bth & Pets Ok

Escape to Lakefront Leisure—Amazing views!

Creekside Cottage

Deluxe Mtn Loft, Oct leaves changing colors.

Dutch Touch Woodstock Cottage

Modern Barn on 12 acres w Sauna, FirePit+swimming

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Rushing Rapids Cottage – a birdwatcher's paradise
Other waterfront vacation rentals

Waterfront Modern Lake Mansfield Retreat

Zen River Studio

Waterfront oasis in heart of Berkshires

Lake House in the Heart of the Berkshires

Modern and Stylish Country Lakeside Cottage

Cabin 192

Lake Life Luxe

Cabin on Copake Lake, NY.
Quick stats about waterfront rentals in Great Barrington
Total rentals
20 properties
Nightly prices starting at
R1,911 ZAR before taxes and fees
Total number of reviews
960 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Rentals with a patio Great Barrington
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- Waterfront rentals Berkshire County
- Waterfront rentals Massachusetts
- Waterfront rentals United States
- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Thunder Ridge Ski Area
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Mount Greylock Ski Club
- Windham Mountain
- Norman Rockwell Museum
- Wintonbury Hills Golf Course
- Taconic State Park
- Mount Sugarloaf State Reservation
- Opus 40
- Mount Southington Ski Area
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Tom State Reservation
- Hunter Mountain Resort