Family-friendly vacation rentals in Great Barrington

4.99 out of 5 average rating, 366 reviews

Loft in Great Barrington

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

HospitalityLocationComfortCleanlinessIndoor spacesKitchenNearbyQuietDecorSleep qualityAmenitiesViewGetting aroundHikingAccuracyOutdoor spacesBreakfastWalkabilityConditionWifiCheck-inTVBathroomHeatingSkiingCheckoutBikingLayoutLaundryGrillAccessRiverValueAir conditioningParkingNoiseLong stayFamily

Apartment in Great Barrington

A modern bedroom showcases a spacious bed with crisp white linens. Accent lighting frames the walls, and a patterned area rug adds warmth to the space. A compact seating area with stylish benches complements the décor, while an entrance leads to a private bathroom.

4.92 out of 5 average rating, 165 reviews

King Bed | Stylish | 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 *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

CleanlinessComfortLocationDecorNearbyIndoor spacesHospitalitySleep qualityBathroomConditionValueWalkabilityAccuracyPetsBackyardCheck-inOutdoor spacesKitchenQuietPoolGetting aroundCheckoutAccessAmenitiesSkiingTVHikingNoiseAir conditioningParkingLaundryFamilyWifiHeatingSolo travelLong stayBreakfastShared spaces

Guest suite in Great Barrington

A spacious bedroom features a large bed adorned with light bedding and a folded blanket. A shelf holds decorative items alongside a serene figure. Natural light enters through sliding glass doors, leading to an outdoor patio area. A standing fan is placed nearby.

4.99 out of 5 average rating, 135 reviews

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

CleanlinessHospitalityLocationWalkabilityComfortIndoor spacesSleep qualityKitchenAmenitiesBathroomNearbyQuietDecorViewOutdoor spacesAccuracyParkingGetting aroundFamilyConditionAccessLaundryCheck-inHikingLayoutHeatingWifiNoiseBikingSkiingTVLong stayBreakfastBackyardValueAir conditioning

Guesthouse in Great Barrington

A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.

4.95 out of 5 average rating, 172 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

HospitalityCleanlinessLocationComfortIndoor spacesKitchenNearbyDecorFamilySleep qualityQuietAccuracyWalkabilityAmenitiesCheck-inSkiingGetting aroundBathroomPetsHikingConditionValueOutdoor spacesLaundryLayoutCheckoutAir conditioningLong stayHeatingParkingWifiBiking

4.99 out of 5 average rating, 313 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

HospitalityLocationCleanlinessComfortIndoor spacesDecorFamilyOutdoor spacesAccuracyKitchenAmenitiesNearbyBathroomHikingSleep qualityQuietCheck-inSkiingLayoutGetting aroundHeatingViewConditionBackyardCheckoutHot tubTVWifiWalkabilityNoiseGrillLong stayAccessValueLaundry

4.99 out of 5 average rating, 137 reviews

A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.

Bungalow in Egremont

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

LocationCleanlinessHospitalityComfortIndoor spacesNearbyOutdoor spacesFamilyDecorSleep qualityAmenitiesKitchenQuietWalkabilityAccuracyHikingLayoutBackyardPetsSkiingBathroomCheck-inGetting aroundTVGrillHeatingRiverConditionAccessWifiLaundryLong stayBreakfastViewCheckout

Treehouse in New Marlborough

The treehouse is nestled among tall trees, surrounded by a gravel area. A cozy seating arrangement with several chairs is positioned near a fire pit, offering an inviting outdoor space. A shaded canopy provides shelter, enhancing the serene forest setting.

4.91 out of 5 average rating, 170 reviews

Berkshire Treehouse Retreat

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

LocationHospitalityComfortOutdoor spacesIndoor spacesFamilyAccessDecorBathroomSleep qualityNearbyGrillGetting aroundRiverAccuracyCleanlinessPetsHeatingKitchenAmenitiesHikingViewWalkabilityValueParksQuietCheck-inParkingConditionNoiseCheckoutAir conditioning

Tiny home in New Marlborough

4.94 out of 5 average rating, 190 reviews

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

HospitalityLocationComfortCleanlinessOutdoor spacesIndoor spacesNearbySleep qualityHikingViewPetsAmenitiesAccuracyKitchenFamilyCheck-inBathroomQuietDecorWifiRiverGetting aroundAccessAir conditioningSolo travelWalkabilityLong stayConditionValueSkiingTVGrillParksHeatingParkingBackyardHot tubNoise

A sunlit seating area features a black couch centered on a wooden coffee table. Two patterned chairs are positioned opposite the couch, creating a cozy conversation space. Natural light filters through multiple windows adorned with blinds, illuminating the polished hardwood floor.

4.94 out of 5 average rating, 139 reviews

GB at your doorstep

Our home is in the heart of vibrant downtown Great Barrington, just steps from the River Walk. Stroll a block to the vibrant shops, eateries, farmer's market, and historic Mahaiwe Theater. It's a quick 20 minute drive to the world class music at Tanglewood and the theater productions at Shakespeare & Co. Winter sports enthusiasts will be 5 minutes to Ski Butternut and 15 minutes to Catamount Ski Mountain. Relaxation at Lake Mansfield is only minutes away by car.

LocationHospitalityWalkabilityCleanlinessKitchenComfortFamilyIndoor spacesNearbyDecorQuietSleep qualityCheck-inAmenitiesHikingGetting aroundConditionAccuracyOutdoor spacesAir conditioningSkiingBathroomParkingRiverGrillTVLayoutWifiCheckoutBackyardNoiseValueBikingLaundryLong stayAccess

Cottage in Great Barrington

A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.

4.94 out of 5 average rating, 217 reviews

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

HospitalityLocationComfortCleanlinessNearbySleep qualityIndoor spacesQuietDecorAccuracyAmenitiesGetting aroundCheckoutCheck-inHikingFamilyOutdoor spacesKitchenViewBackyardAccessConditionBathroomEV chargingTVLong stayValueSkiingLayoutHeatingSolo travelPoolAir conditioning

Cottage in Great Barrington

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

4.93 out of 5 average rating, 350 reviews

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

Hot tubLocationHospitalityIndoor spacesBathroomComfortOutdoor spacesNearbyHikingCleanlinessAmenitiesDecorKitchenQuietAccuracySleep qualityTVWalkabilityCheck-inGetting aroundBackyardConditionAir conditioningValueSkiingLayoutFamilyCheckoutGrillViewWifiPetsBreakfastRiverBeachAccessBikingHeatingParking

4.97 out of 5 average rating, 158 reviews

A bright bedroom features a spacious bed with neutral bedding, framed by wooden walls and beams. Natural light fills the room through a large window, showcasing a glimpse of the outdoor area. A small side table and a decorative plant complement the simple, serene design.

Cabin in Chatham

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

HospitalityLocationDecorComfortIndoor spacesKitchenCleanlinessSleep qualityViewNearbyOutdoor spacesConditionQuietFamilyBathroomAmenitiesHikingGetting aroundAccuracyWifiWalkabilityCheck-inGrillValueHeatingCheckoutLayoutLong stayTVParksLaundryBreakfastNoiseAir conditioningBiking

Popular amenities for Great Barrington family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 307 reviews

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Monterey

Jaw dropping mountain & lake views

ViewHospitalityComfortDecorIndoor spacesCleanlinessLocationFamilyKitchenHot tubSleep qualityOutdoor spacesAccuracyGetting aroundNearbyAmenitiesLayoutBathroomSkiingHikingCheck-inConditionQuietHeatingBackyardAccessCheckoutShared spacesTVGrillWifiValueParksLaundryWalkability

A hot tub sits on a polished wooden deck, surrounded by greenery. Soft lighting from string lights illuminates the area. A colorful striped pillow rests on a lounge chair, with a patterned plate and drink placed nearby, creating a relaxing outdoor retreat.

4.94 out of 5 average rating, 144 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

Hot tubLocationCleanlinessHospitalityComfortKitchenNearbyAmenitiesSleep qualityDecorIndoor spacesAccuracyFamilyBackyardSkiingQuietAccessConditionBathroomGetting aroundHikingOutdoor spacesPetsCheck-inGrillParkingNoiseValueAir conditioningHeatingLong stayCheckout

4.97 out of 5 average rating, 101 reviews

Cabin in East Nassau

Luxury Cabin - Fall Foliage & Autumn Adventures

HospitalityViewCleanlinessIndoor spacesOutdoor spacesKitchenAmenitiesComfortHot tubLocationFamilyDecorNearbyAccuracyBathroomPetsHeatingLayoutGrillSkiingHikingConditionTVQuietBackyardSleep qualityGetting aroundAccessCheckoutBikingCheck-in

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

Hot tubLocationHospitalityComfortFamilyIndoor spacesKitchenOutdoor spacesCleanlinessAmenitiesSleep qualityNearbyHikingAccuracyGetting aroundQuietSkiingGrillTVViewWifiCheck-inBackyardDecorConditionLayoutWalkabilityBathroomBeachAir conditioningCheckoutAccessHeatingRiverValueParksLaundryLong stayBikingParkingNoise

4.99 out of 5 average rating, 371 reviews

A tiny home features a private hot tub on the deck, illuminated by soft LED lights. The structure is surrounded by natural wood paneling, with doors leading into the cozy interior, where warm light spills out, creating an inviting ambiance.

Tiny home in Chatham

Boutique TINY home+private HOT TUB-walk to Main St

Indoor spacesKitchenSolo travel

4.99 out of 5 average rating, 153 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

KitchenIndoor spacesLaundry

4.95 out of 5 average rating, 130 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

KitchenFamilySleep quality

4.96 out of 5 average rating, 118 reviews

The kitchen features deep black cabinetry paired with warm wood countertops. A window above the sink allows natural light to illuminate the floral wallpaper. Modern fixtures and a stylish faucet enhance the space, offering a functional area for meal preparation.

Cabin in Hudson

Cozy Grove Luxury Cabin

FamilyIndoor spacesCleanliness

Family- and pet-friendly home rentals

Cottage in Great Barrington

A rustic cottage is surrounded by snow-covered ground and tall trees. The structure features dark wood siding with green window frames and a welcoming front porch. A fenced area is visible in the foreground, enhancing the sense of privacy and tranquility.

4.91 out of 5 average rating, 276 reviews

Cottage on Scenic Road

KitchenFamilyGetting around

4.96 out of 5 average rating, 111 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

Indoor spacesFamilyCheckout

4.95 out of 5 average rating, 187 reviews

An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.

Home in Stockbridge

Bright Stockbridge country home, near everything!

Indoor spacesFamilyBathroom

4.97 out of 5 average rating, 167 reviews

An A-frame cabin is nestled within a forested area, featuring a striking black exterior and a sloping roof with wooden accents. Tall grasses and shrubs surround the entrance, creating a natural backdrop. A gravel path leads to the cabin, framed by lush greenery.

Cabin in Saugerties

Luxury A-Frame Cabin in the Woods with Sauna

FamilyKitchenPets

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.

KitchenFamilyBeach

A charming red house is set against a backdrop of lush greenery. The stone chimney adds a rustic touch, while outdoor seating is arranged on the lawn. A small tower feature enhances the unique architectural design, creating an inviting outdoor space.

4.91 out of 5 average rating, 139 reviews

Never too early to book for the Holidays & NYE!

FamilyIndoor spacesView

Cabin in Litchfield County

A cozy living area features a brown leather sofa with white throw pillows, positioned beside a window that allows natural light. A wooden coffee table sits atop a blue and white woven rug, complemented by a comfortable armchair. Shelves display decorative items and fresh flowers add a welcoming touch.

4.94 out of 5 average rating, 154 reviews

Blackberry Cottage

KitchenFamilyHeating

A light-filled open living area features a large sectional sofa arranged around a coffee table, with a soft rug underfoot. Two expansive windows provide views of the greenery outside. A dining space with high chairs is visible in the background, enhancing the inviting atmosphere.

4.99 out of 5 average rating, 129 reviews

Private Home in The Berkshires (New Hot Tub!)

KitchenIndoor spacesGetting around

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 109 reviews

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

HospitalityPoolComfortKitchenIndoor spacesLocationDecorFamilyCleanlinessNearbyOutdoor spacesAmenitiesConditionSkiingAccuracyBathroomSleep qualityGrillGetting aroundPetsHikingQuietTVLayoutWifiCheckoutAir conditioningCheck-inHeatingBackyardBikingParksLong stayAccessShared spacesValue

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

ViewHospitalityPoolLocationComfortCleanlinessFamilyGetting aroundNearbyKitchenIndoor spacesSleep qualityCheck-inAccuracyAmenitiesOutdoor spacesRiverCheckoutDecorConditionQuietWifiNoiseTVGrillHikingLaundryWalkabilityBackyardAccessParksLayoutParkingSolo travelAir conditioning

4.96 out of 5 average rating, 391 reviews

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

PoolHospitalityLocationKitchenOutdoor spacesPetsComfortIndoor spacesCleanlinessDecorAmenitiesBathroomBackyardFamilySleep qualityNearbyAccuracyQuietGetting aroundCheck-inGrillViewTVHot tubWifiHeatingHikingConditionCheckoutLaundryValueLayoutParksAccessAir conditioningLong stayBikingWalkabilityNoiseShared spaces

4.98 out of 5 average rating, 100 reviews

A peaceful backyard is featured, showcasing two green swings suspended from a sturdy frame. The grassy lawn is bordered by a wooden fence, and a relaxing seating area with a lounge chair is visible in the background, surrounded by greenery and trees.

Home in Catskill

Catskill Village Ski Hike Lake Pet Main St Pool

FamilyHospitalityLocationCleanlinessWalkabilityBackyardComfortKitchenIndoor spacesPetsNearbyConditionAmenitiesSleep qualityAccuracyPoolDecorOutdoor spacesBathroomGetting aroundSkiingHikingLayoutQuietNoiseValueCheck-inParksGrillLong stayAir conditioning

4.95 out of 5 average rating, 169 reviews

A modern tiny house is surrounded by tall trees, with warm light emanating from its large windows. The sleek black exterior contrasts with the natural greenery, creating a blend of contemporary design and serene nature. The rising dusk hints at a tranquil evening.

Tiny home in Ghent

Country Getaway Tiny House in woods w/Pool/Sauna

HospitalityPoolLocationNearbyPetsIndoor spacesCleanlinessComfortOutdoor spacesHikingSleep qualityQuietAccuracyDecorBathroomKitchenAmenitiesWalkabilityConditionGetting aroundViewHeatingFamilyGrillWifiSolo travelBackyardShared spacesValueLayoutAir conditioningCheck-in

Superhost

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

Home in Hudson

4.94 out of 5 average rating, 194 reviews

Hudson getaway w/ hot tub+ plunge pool on 20 acres

Hot tubHospitalityCleanlinessLocationComfortIndoor spacesKitchenOutdoor spacesFamilyNearbyAmenitiesPoolSleep qualityConditionDecorAccuracyGetting aroundTVQuietBathroomCheck-inBackyardHikingAccessValueCheckoutGrillLaundryAir conditioningSkiingLayoutWifiViewLong stayBreakfastRiverHeatingWalkabilityNoise

4.95 out of 5 average rating, 109 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

HospitalityFamilyIndoor spacesLocationOutdoor spacesViewComfortAccuracyKitchenBeachSleep qualityCleanlinessBackyardHot tubAmenitiesBathroomLayoutDecorConditionNearbyGetting aroundAccessSkiingQuietWalkabilityCheck-inGrillCheckoutValueHikingHeatingLaundryPoolAir conditioning