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Holiday rentals with lake access in Great Barrington

Find and book unique lake access rentals on Airbnb

Quick stats about holiday rentals with lake access in Great Barrington

  • Total holiday rentals

    Explore 30 holiday rentals in Great Barrington

  • Nightly prices starting at

    Great Barrington holiday rentals start at $128 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,950 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Great Barrington holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Great Barrington rentals

  • 4.8 Average rating

    Great Barrington stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated rentals with lake access in Great Barrington

Guests agree: these rentals with lake access are highly rated for location, cleanliness and more.

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Top guest favourite
A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.
Cottage in Becket
4.95 out of 5 average rating, 317 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Outdoor spacesViewCondition

Superhost
A spacious living room features a large U-shaped leather couch and a central ottoman, offering seating for several guests. Natural light pours through multiple windows, highlighting the wooden walls and stone accents. The kitchen area is visible in the background, enhancing the open layout.
Home in Great Barrington
4.85 out of 5 average rating, 137 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!

ViewOutdoor spacesKitchen

Guest favourite
A serene pond reflects the surrounding greenery, with kayaks resting on the shore. A cozy cabin is visible in the background, framed by trees. The tranquil setting invites outdoor activities such as swimming or fishing, creating a peaceful natural atmosphere.
Cabin in Colebrook
4.95 out of 5 average rating, 128 reviews

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. All natural 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 n walk the trail around the pond, have campfires outside in firepit! Clean and no crazy rules. Surrounded by nature! Private Great WIFI! Close to ski resorts, dispensaries and amazing Berkshires! 🦉

Outdoor spacesViewFamily

Guest favourite
An inviting bedroom is adorned with warm knotty pine walls and features a queen bed with decorative pillows. Two windows allow natural light to fill the space, with bedside lamps providing additional illumination. A cozy ottoman sits at the foot of the bed, complementing the rustic decor.
Cabin in Copake Lake
4.93 out of 5 average rating, 270 reviews

Cabin in Woods w/ Lake Access & *private* Hot Tub!

Don't miss your opportunity for a spring adventure at this cozy, secluded cabin with its own private hot tub and lake access! Welcome to Cabin on Hillside, a peaceful haven from the stresses of daily life. Situated in the charming town of Copake Lake, you get all the fun of a quaint lakeside community with the solitude of a wooded retreat. Whether you are looking for outdoor adventures, trips into town, or a peaceful homestay, this cabin provides it all! Come visit! Your oasis awaits!

ViewOutdoor spacesBeach

Guest favourite
Cabin in East Nassau
4.97 out of 5 average rating, 101 reviews

Luxury Cabin - Fall Foliage & Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

NearbyOutdoor spacesQuiet

Guest favourite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham
4.96 out of 5 average rating, 111 reviews

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

Outdoor spacesViewComfort

Top guest favourite
A quaint lakeside cottage features large windows for scenic views and a deck with outdoor seating. A grill is positioned nearby for easy outdoor cooking. The property is framed by lush greenery, enhancing the natural setting by the water's edge.
Home in Becket
5.0 out of 5 average rating, 113 reviews

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Outdoor spacesViewAccess

Guest favourite
A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.
Cabin in Town of Hillsdale
4.91 out of 5 average rating, 128 reviews

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

ViewNearbyComfort

Guest favourite
A spacious log cabin with a metal roof is surrounded by trees. The front porch is lined with a railing, and large windows invite natural light. A gravel driveway leads up to the cabin, with a small shed visible to the side.
Cabin in Monterey
4.94 out of 5 average rating, 308 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

NearbyOutdoor spacesAccuracy

Top guest favourite
Home in Monterey
4.96 out of 5 average rating, 230 reviews

Beautiful family home, Hike, Fireplace, Sleeps 12

Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * Butternut ski Mountain 15 mins * Roaring fireplace & free firewood * Outdoor fire pit * Great Hikes from the house * Pets welcome * Fast Wifi - Fiber * Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Jacobs Pillow & Tanglewood 20 mins * Fishing, kayaking & Swimming Lake 5 mins

NearbyOutdoor spacesCheck-in

Guest favourite
Home in Becket
4.95 out of 5 average rating, 130 reviews

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

ViewNearbyIndoor spaces

Guest favourite
A newly built house is surrounded by lush greenery, featuring a spacious deck with comfortable seating. The exterior showcases a combination of blue siding and large windows, allowing natural light to flow indoors. A stone patio with seating is visible, enhancing the outdoor living experience.
Home in New Marlborough
4.89 out of 5 average rating, 152 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.

Outdoor spacesNearbyAccuracy

Popular amenities for lake access rentals in Great Barrington

KitchenWifiPoolFree parking on premisesAir conditioning

Lake access house rentals

Superhost
Home in Hudson
4.94 out of 5 average rating, 143 reviews

Designer Home, Hot Tub, Private Yard, & Projector

NearbyViewAccuracy

Top guest favourite
A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.
Home in Ghent
4.89 out of 5 average rating, 376 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Outdoor spacesViewWifi

Top guest favourite
A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.
Home in Catskill
4.95 out of 5 average rating, 253 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

ViewOutdoor spacesCondition

Guest favourite
Home in Craryville
4.85 out of 5 average rating, 170 reviews

Copake Lake Artist Cottage with Dock and Kayaks

ViewOutdoor spacesTV

Top guest favourite
The tranquil lake reflects a soft sunrise, showcasing a palette of warm hues and gentle ripples. A dock and small boats are visible on the water, framed by the serene landscape of trees along the shore.
Home in Otis
4.95 out of 5 average rating, 175 reviews

Idyllic family retreat - spacious lake home,

Outdoor spacesNearbyHospitality

Top guest favourite
A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.
Home in Rhinebeck
4.98 out of 5 average rating, 130 reviews

Slate Cabin - Stylish Country Escape x Rhinebeck

ViewNearbyCleanliness

Superhost
Home in Becket
4.91 out of 5 average rating, 176 reviews

Lake front retreat - Stylish Berkshire home

NearbyViewEV charging

Top guest favourite
The charming exterior of a renovated farmhouse features a spacious front porch with a red bench and hanging flower baskets. Large windows allow natural light to fill the entryway, while lush green grass and trees frame the property.
Home in Canaan
4.99 out of 5 average rating, 118 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Outdoor spacesViewBack garden

Apartment rentals with lake access

Top guest favourite
A spacious front porch is framed by white columns and features two seating areas. Lush greenery encompasses the porch, with a flowering rhododendron bush in the foreground. The blue sky is dotted with clouds, enhancing the inviting atmosphere of the outdoor space.
Flat in New Lebanon
4.97 out of 5 average rating, 121 reviews

Airy apartment at the old boarding house

NearbyOutdoor spacesParking

Top guest favourite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Flat in Coxsackie
4.99 out of 5 average rating, 162 reviews

Hudson River Beach House

ViewOutdoor spacesSkiing

Top guest favourite
A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.
Flat in Otis
4.96 out of 5 average rating, 130 reviews

Enjoy every season the Berkshires have to offer.

ViewOutdoor spacesLocation

Top guest favourite
An open layout kitchen and living area is highlighted by exposed brick walls and hardwood flooring. A modern kitchen is equipped with stainless steel appliances, while a comfortable brown leather sofa is accompanied by a coffee table. Natural light enters through a window centered in the room.
Flat in Hudson
5.0 out of 5 average rating, 120 reviews

Hip Warren Street Apartment

NearbyViewKitchen

Guest favourite
A welcoming living area is highlighted by natural light streaming in through large windows. A comfortable sectional sofa is paired with two patterned chairs and a round woven coffee table, creating an inviting space for relaxation. A television is positioned on an elegant media console.
Flat in Craryville
4.91 out of 5 average rating, 176 reviews

Captain's Quarters at Mickey's Marina

ViewOutdoor spacesHospitality

Guest favourite
The exterior of a rustic cottage is presented, featuring large windows that allow natural light to fill the interior. A wooden deck leads to a glass-paned door, framed by light-colored siding and contrasting trim. Trees and greenery are visible in the background.
Flat in Salt Point
4.86 out of 5 average rating, 208 reviews

Arcady - Modern, 1br cottage

NearbyOutdoor spacesIndoor spaces

Guest favourite
A bright and inviting living room features a floral-patterned couch and large windows adorned with green curtains. Decorative plant stands filled with various plants enhance the space, while a stained glass light fixture casts a warm glow over the area. A cozy atmosphere is created with soft lighting.
Flat in Winchester
4.91 out of 5 average rating, 422 reviews

Gateway to the Berkshires

ViewNearbyRiver

Top guest favourite
A spacious neo-colonial mansion features a wraparound porch and multiple gabled roofs. The exterior is painted in a warm gray tone, complemented by manicured greenery and decorative landscaping. The building showcases large windows and a well-defined entrance, creating an inviting atmosphere.
Flat in Hudson
4.92 out of 5 average rating, 216 reviews

Private Elegant 1BR Apt One Block to Warren St.

Outdoor spacesNearbyCondition

Lake access cottage rentals

Top guest favourite
An aerial view showcases a lakefront cottage with a warm-toned roof, surrounded by lush greenery. Two blue kayaks sit on the water, while a stone patio features a dining area. A fire pit adds to the outdoor space, blending with a wooden boat dock.
Cottage in Livingston
4.97 out of 5 average rating, 140 reviews

Waterlily Lakehouse - Modern+Waterfront+Retreat

NearbyViewLaundry

Guest favourite
A spacious deck overlooks the lake, featuring a glass dining table surrounded by yellow chairs. A lounge chair is positioned nearby. A bright yellow umbrella provides shade, and trees frame the scene, accentuating the sunset sky in the background.
Cottage in Craryville
4.82 out of 5 average rating, 136 reviews

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

ViewOutdoor spacesQuiet

Top guest favourite
A serene lake reflects the colors of twilight, with calm waters mirroring the darkening sky. A crescent moon is visible, while silhouettes of trees line the horizon. The scene captures the tranquil beauty of dusk over the peaceful landscape.
Cottage in Hinsdale
4.99 out of 5 average rating, 167 reviews

Cozy Cottage in the Berkshires

Outdoor spacesViewLocation

Guest favourite
The living room features exposed wooden beams and warm hardwood flooring. A spacious seating area is centered on a large area rug, surrounded by colorful floor rugs. Framed artwork adorns the walls, while natural light filters in through window treatments.
Cottage in Catskill
4.94 out of 5 average rating, 124 reviews

Cozy Catskill Cottage

Outdoor spacesNearbyCheckout

Superhost
An open-concept living space features a modern kitchen with stainless steel appliances and a dining area with a wooden table. A cozy seating area includes a gray sofa positioned near a fireplace. Natural light filters through sheer curtains, creating an inviting ambiance.
Cottage in Kingston
4.89 out of 5 average rating, 140 reviews

Modern, Lakeside Cottage

ViewOutdoor spacesTV

Guest favourite
A tranquil outdoor scene showcases several wooden Adirondack chairs arranged around a fire pit, facing a calm body of water. The surrounding trees exhibit vibrant autumn colors, reflecting beautifully in the water, creating a serene natural atmosphere.
Cottage in Hudson
4.84 out of 5 average rating, 154 reviews

Hudson area waterfront-fish, kayak, farm visits!

NearbyViewFamily

Guest favourite
Cottage in Egremont
4.98 out of 5 average rating, 55 reviews

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

NearbyViewCondition

Guest favourite
Cottage in New Marlborough
4.92 out of 5 average rating, 52 reviews

Cottage near lake Explore the Berkshires, Pets OK!

NearbyOutdoor spacesWalkability

When is the best time to visit Great Barrington?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$384 SGD$384 SGD$384 SGD$371 SGD$384 SGD$416 SGD$510 SGD$504 SGD$388 SGD$384 SGD$405 SGD$470 SGD
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