Holiday rentals with lake access in Great Barrington

4.95 out of 5 average rating, 317 reviews

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

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.

NearbyOutdoor spacesParks

4.85 out of 5 average rating, 137 reviews

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

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!

NearbyOutdoor spacesCheck-in

4.89 out of 5 average rating, 250 reviews

Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

ViewOutdoor spacesSleep quality

4.97 out of 5 average rating, 101 reviews

Cabin in East Nassau

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!

Outdoor spacesNearbySleep quality

4.96 out of 5 average rating, 112 reviews

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

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 spacesNearbyPets

5 out of 5 average rating, 113 reviews

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

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.

ViewNearbyWalkability

4.91 out of 5 average rating, 128 reviews

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 Hillsdale

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.

NearbyOutdoor spacesWi-Fi

4.94 out of 5 average rating, 308 reviews

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

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.

ViewNearbyRiver

4.96 out of 5 average rating, 231 reviews

Home in Monterey

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 spacesCheckout

4.94 out of 5 average rating, 132 reviews

Home in Becket

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

Outdoor spacesViewComfort

4.89 out of 5 average rating, 152 reviews

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

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 spacesNearbyBarbecue

4.92 out of 5 average rating, 144 reviews

Home in Hudson

Designer Home, Hot Tub, Private Yard, & Projector

A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

ViewNearbyValue

Popular amenities for Great Barrington lake access rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Lake access house rentals

4.94 out of 5 average rating, 153 reviews

A charming house is set within a wooded area, with autumn foliage creating a colorful backdrop. The exterior features a stone fireplace and expansive windows, offering glimpses of the serene environment. Nearby, a fire pit with seating is positioned on the green lawn.

Home in Becket

Beautiful, quiet and cozy home in Becket!

NearbyOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 130 reviews

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

Slate Cabin - Stylish Country Escape x Rhinebeck

Outdoor spacesViewAccuracy

4.99 out of 5 average rating, 130 reviews

A modern white house, originally an ice house, sits in a grassy setting with large windows reflecting the sunset. Adirondack chairs are arranged around a fire pit, promoting outdoor gatherings. A wooden deck extends from one side, enhancing accessibility to the inviting yard.

Home in Hudson

Hudson Ice House, 25 acre retreat w/ pond & views!

NearbyViewLong stay

4.99 out of 5 average rating, 118 reviews

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

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

NearbyViewComfort

4.98 out of 5 average rating, 48 reviews

A modern house is presented with a grey exterior under a clear blue sky. A spacious deck features a sectional sofa and an umbrella near large rocks and vibrant greenery. Expansive windows allow ample natural light into the interior.

Home in Sandisfield

Waterfront oasis in heart of Berkshires

ViewOutdoor spacesHiking

4.89 out of 5 average rating, 376 reviews

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

Modern Barn on 12 acres w Sauna, FirePit+swimming

ViewOutdoor spacesTV

4.95 out of 5 average rating, 175 reviews

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

Idyllic family retreat - spacious lake home,

NearbyViewPool

4.93 out of 5 average rating, 28 reviews

Home in Great Barrington

Lovely house in the Berkshires

Outdoor spacesNearbyLayout

Lake access apartment rentals

Apartment in Great Barrington

4.76 out of 5 average rating, 25 reviews

Writer/Reader Retreat: Summer or Fall 2026

NearbyOutdoor spacesSleep quality

4.86 out of 5 average rating, 208 reviews

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.

Apartment in Salt Point

Arcady - Modern, 1br cottage

NearbyViewPets

Apartment in Great Barrington

A bright sunroom features large windows that allow natural light to illuminate the space. A gray and white patterned rug lies on the floor, complementing a cozy seating area with yellow cushions. A green dining table with chairs and potted plants add a touch of color.

4.93 out of 5 average rating, 42 reviews

Zen River Studio

NearbyViewAir conditioning

5 out of 5 average rating, 120 reviews

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.

Apartment in Hudson

Hip Warren Street Apartment

NearbyViewAccuracy

4.9 out of 5 average rating, 39 reviews

A spacious living area is highlighted by a textured wall and a modern light fixture. A cozy gray sofa is paired with a soft throw blanket, while a wooden coffee table sits in front. A dining area with multiple chairs and a cabinet is visible in the background.

Apartment in Red Hook

The Perfect Place

NearbyAir conditioningLocation

4.99 out of 5 average rating, 164 reviews

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.

Apartment in Coxsackie

Hudson River Beach House

ViewOutdoor spacesCheckout

4.91 out of 5 average rating, 422 reviews

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.

Apartment in Winchester

Gateway to the Berkshires

Outdoor spacesNearbyCheckout

4.96 out of 5 average rating, 130 reviews

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.

Apartment in Otis

Enjoy every season the Berkshires have to offer.

Outdoor spacesViewLocation

Lake access cottage rentals

4.85 out of 5 average rating, 61 reviews

The bright and airy kitchen and dining area features high ceilings and modern fixtures. A wooden table with stylish chairs sits at the center, flanked by a sleek kitchen with stainless steel appliances. Natural light flows in through windows, enhancing the clean and open space.

Cottage in Copake

Lakefront Retreat on Robinson Pond

ViewNearbyFamily

4.89 out of 5 average rating, 18 reviews

Cottage in Pittsfield

Pine & Paddle | Pond Access • Kayaks

NearbyViewPets

4.84 out of 5 average rating, 154 reviews

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

Hudson area waterfront-fish, kayak, farm visits!

Outdoor spacesViewGetting around

4.94 out of 5 average rating, 124 reviews

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

Cozy Catskill Cottage

NearbyOutdoor spacesAmenities

4.97 out of 5 average rating, 141 reviews

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

Waterlily Lakehouse - Modern+Waterfront+Retreat

Outdoor spacesNearbyCondition

4.98 out of 5 average rating, 47 reviews

Cottage in East Otis

The lake house

NearbyViewWi-Fi

4.82 out of 5 average rating, 136 reviews

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

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

Outdoor spacesViewFamily