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Lake house holiday rentals in Boys & Girls Club of the Berkshires Ice Rink

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Top-rated lakehouse rentals in Boys & Girls Club of the Berkshires Ice Rink

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Superhost
Home in Becket

Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

ValueLocationShared spaces

4.92 out of 5 average rating, 180 reviews
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

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

ValueFamilyCheckout

4.99 out of 5 average rating, 119 reviews
Guest favourite
A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.
Home in Canaan

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

ValueLocationView

4.91 out of 5 average rating, 187 reviews
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

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.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 116 reviews
Top Guest favourite
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

LocationFamilyAmenities

4.96 out of 5 average rating, 233 reviews
Top Guest favourite
The spacious kitchen features an island with a wood countertop and built-in storage. Mint green cabinetry offers a serene ambiance. Natural light flows through large windows, illuminating the dining area with a wooden table and cozy seating, creating an inviting space for gatherings.
Home in Ghent

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres

At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

FamilyLocationCondition

4.98 out of 5 average rating, 134 reviews
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

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.

LocationValueHiking

4.95 out of 5 average rating, 175 reviews
Guest favourite
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

FamilyValueView

4.94 out of 5 average rating, 134 reviews
Superhost
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

ValueLocationPets

4.91 out of 5 average rating, 149 reviews
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

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.

ValueFamilyCleanliness

4.89 out of 5 average rating, 152 reviews
Guest favourite
A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.
Home in Stockbridge

Rabbit Run in the heart of Stockbridge Village

Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.

FamilyValueSleep quality

4.89 out of 5 average rating, 126 reviews
Guest favourite
Aerial view of Lake Garfield, with smooth waters reflecting the surrounding greenery. Two kayaks are visible, gliding across the lake near a small motorboat. Lush trees line the shoreline, with a private dock and patio area partially seen along the bank.
Home in Monterey

Forest Hollow | Waterfront • Kayaks • Wood Stove

Take a step out of everyday life and enjoy some rest and relaxation at this cozy home on the lake nestled in the hills of The Berkshires. Lay out on the docks, swim in the water, enjoy the foliage and unwind by the fireplace after a day of skiing! This place really has all the comforts anyone may need after a day spent enjoying the outdoors in The Berkshires. Come see for yourself!

LocationValueKitchen

4.85 out of 5 average rating, 99 reviews

Popular amenities for Boys & Girls Club of the Berkshires Ice Rink lakehouse rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront lakehouse rentals

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

HEAVEN ON EARTH - Hudson Riverfront Home

LocationFamilyBreakfast

4.95 out of 5 average rating, 256 reviews
Top Guest favourite
A spacious deck is shown with lightly stained wooden flooring and several wooden chairs arranged in a circle. In the background, a large two-story home is visible, surrounded by greenery and trees under a clear blue sky.
Home in Averill Park

Lakefront Retreat: Bald Eagles & Huge Windows

ValueLocationCleanliness

5.0 out of 5 average rating, 112 reviews
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

Slate Cabin - Stylish Country Escape x Rhinebeck

LocationFamilyOutdoor spaces

4.98 out of 5 average rating, 130 reviews
Top Guest favourite
A hammock is suspended between two large trees, offering a serene spot to relax by the water. Below, colorful kayaks rest on the grassy shore, framing the edge of Glass Lake, which reflects the surrounding greenery and blue sky.
Home in Averill Park

Lake House in Averill Park, NY

FamilyValueQuiet

4.97 out of 5 average rating, 202 reviews
Guest favourite
An open-concept living area features a comfortable sectional sofa, wooden coffee table, and bright skylights allowing natural light to fill the space. A modern kitchen with a large island and bar seating complements the airy atmosphere, providing a seamless flow to the dining area and views outside.
Home in Otis

Direct Lakefront Home on Otis Reservoir Giant Yard

ValueFamilyAmenities

4.96 out of 5 average rating, 134 reviews
Guest favourite
The living room features large windows offering views of the river and surrounding trees. A blue sofa and a beige tufted couch are positioned around a wooden coffee table, while a colorful area rug adds warmth to the space. Bright yellow walls enhance the inviting atmosphere.
Home in New Paltz

Welcome to The Boathouse! Waterfront/Boats/Hot tub

LocationFamilyHeating

4.92 out of 5 average rating, 395 reviews
Top Guest favourite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford

Vermont Mirror House

FamilyLocationAccess

4.95 out of 5 average rating, 156 reviews
Top Guest favourite
A serene view features a private in-ground pool surrounded by lounge chairs, each shaded by black umbrellas. Lush green trees border the backyard, and a red house is visible in the background, completing the outdoor vacation atmosphere.
Home in Canaan

Berkshire Lake House, gunite pool, Chef's Kitchen

FamilyLocationSkiing

4.99 out of 5 average rating, 101 reviews

Pet-friendly lake house rentals

Top Guest favourite
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!

ValueLocationWi-Fi

4.94 out of 5 average rating, 154 reviews
Guest favourite
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

LocationFamilyLayout

4.85 out of 5 average rating, 138 reviews
Top Guest favourite
A multi-story wooden house is set against a backdrop of lush green trees. Colorful flowering bushes, primarily in shades of pink, enhance the natural landscape, while a glass solarium extends from one side of the house, showcasing outdoor living space.
Home in New Hartford

Private Woodland Sanctuary—3 mins to a lake beach!

ValueLocationOutdoor spaces

4.97 out of 5 average rating, 118 reviews
Top Guest favourite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens

Private lakefront home, hot tub & resort amenities

LocationFamilyDecor

4.95 out of 5 average rating, 192 reviews
Top Guest favourite
Home in Tannersville

Romantic getaway!3BDR/2BTH-HotTub/Sauna/Fireplace!

FamilyLocationWalkability

4.99 out of 5 average rating, 202 reviews
Guest favourite
Home in Craryville

Copake Lake Artist Cottage with Dock and Kayaks

ValueFamilyKitchen

4.85 out of 5 average rating, 171 reviews
Top Guest favourite
A spacious hot tub is positioned under a wooden pavilion, surrounded by string lights. Water cascades gently inside, with soft lighting reflecting on the surface. In the background, a tranquil view of the lake and nearby seating areas can be seen, inviting relaxation.
Home in Athens

Hudson Valley Lake · Hot Tub · Dock · Games · View

FamilyLocationCleanliness

4.98 out of 5 average rating, 108 reviews
Guest favourite
A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.
Home in East Haddam

Romantic Getaway at The Lake!

FamilyValueTV

4.93 out of 5 average rating, 354 reviews

Private lake house rentals

Top Guest favourite
Home in Pittsfield

Cozy cottage on peaceful pond

LocationFamilyAmenities

5.0 out of 5 average rating, 37 reviews
Top Guest favourite
An aerial view of a lakeside home surrounded by trees showcasing fall foliage. A wooden dock extends into the calm water, with the house positioned amidst lush greenery. The vibrant autumn colors add warmth to the natural setting.
Home in Becket

Fall Foliage Lakefront Retreat - Berkshires

FamilyLocationView

5.0 out of 5 average rating, 46 reviews
Top Guest favourite
Home in New Lebanon

Modernized 1860s Getaway w/ Queechy Lake Passes*

ValueFamilyNearby

5.0 out of 5 average rating, 26 reviews
Guest favourite
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

FamilyLocationOutdoor spaces

4.98 out of 5 average rating, 48 reviews
Guest favourite
A bright living room features a comfortable white sofa and a plush armchair beside a coffee table on a patterned rug. Large windows allow natural light to illuminate the space, while a television is positioned against a wooden accent wall. A potted plant adds a touch of greenery.
Home in Lee

Spacious Central Berkshires Home for Groups

FamilyLocationDecor

4.89 out of 5 average rating, 53 reviews
Top Guest favourite
A warm fire burns within a stone fire pit, with flames flickering against the evening sky. The serene lake reflects the fading light, while a wooden dock is visible in the distance, surrounded by tall reeds and lush greenery.
Home in Lenox

Lakefront Retreat -Private Dock,creek,and Fire pit

FamilyValueCheck-in

4.98 out of 5 average rating, 43 reviews
Guest favourite
A spacious living area features large windows that frame views of the surrounding trees. A cozy sectional sofa and a lounge chair are arranged around a coffee table on a soft area rug, creating an inviting space for relaxation and conversation.
Home in Becket

Berkshires Lakefront Stylish Retreat w/Gameroom

LocationFamilyGetting around

4.98 out of 5 average rating, 47 reviews
Guest favourite
A serene view of a tranquil lake reflects the blue sky and surrounding greenery. The outdoor area includes a wooden deck with seating, a grassy lawn, and boats awaiting exploration. Sunlight glints on the water's surface, enhancing the peaceful atmosphere.
Home in Copake

Lakefront Home • Kayaks • Firepit • Near Skiing

LocationFamilyDecor

4.88 out of 5 average rating, 32 reviews

Destinations to explore