Family-friendly vacation rentals in Great Barrington

Apartment in Great Barrington

A cozy living room features a light sofa and two armchairs flanking a wooden coffee table. A decorative rug with intricate patterns lies beneath. Natural light filters through multiple bay windows, highlighting the serene and vintage-inspired decor.

Walk Everywhere! | Relax in Easy Elegance!

Gracious in-town apartment feels like home: living and dining rooms, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Walk to shops, restaurants, theaters, farmers’ market. Drive to more nearby arts offerings, hiking, skiing, swimming. Spectrum WiFi; please note, there is no TV. Bedrooms are small but with plenty of space to spread out, relax, read, play games or enjoy a meal in the entire apartment. The shared porch is available for morning coffee, evening cocktails or a good book.

KitchenIndoor spacesCleanliness

5.0 out of 5 average rating, 149 reviews

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.

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

KitchenFamilyView

4.91 out of 5 average rating, 178 reviews

Guesthouse in Great Barrington

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.

FamilyIndoor spacesHeating

4.95 out of 5 average rating, 177 reviews

4.99 out of 5 average rating, 143 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.

Indoor spacesKitchenAccess

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.

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.

FamilyKitchenWalkability

4.91 out of 5 average rating, 181 reviews

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, 141 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.

KitchenIndoor spacesRiver

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.

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.

Indoor spacesFamilyHospitality

4.93 out of 5 average rating, 224 reviews

Barn in Town of Hillsdale

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Indoor spacesKitchenAccuracy

4.97 out of 5 average rating, 185 reviews

The charming farmhouse features a covered porch with seating, surrounded by a vibrant garden filled with colorful flowers. Solar panels are visible on the roof, while a grassy area and a small fire pit enhance the outdoor space, inviting relaxation in a natural setting.

5.0 out of 5 average rating, 116 reviews

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Indoor spacesKitchenLocation

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.

Cottage on Scenic Road

NOTE!: As of Sept 2026 the wood stove is temporarily out of service and requires replacement. Please do not plan to be able to use the wood stove; I'll remove this note when the replacement is complete. One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf.

FamilyIndoor spacesView

4.91 out of 5 average rating, 281 reviews

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.

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.

FamilyKitchenNearby

4.94 out of 5 average rating, 355 reviews

The kitchen features light-colored cabinetry with black hardware, complemented by a wood countertop. A refrigerator and an oven with a stovetop are included. A dining table with light wooden chairs is positioned nearby, and a rug adds texture to the hardwood flooring.

4.97 out of 5 average rating, 141 reviews

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

KitchenFamilyCleanliness

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, 311 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

Indoor spacesFamilyAccess

4.95 out of 5 average rating, 313 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

KitchenIndoor spacesBiking

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.

4.95 out of 5 average rating, 146 reviews

Best of the Berkshires + Hot Tub by Evergreen Home

KitchenFamilySleep quality

4.97 out of 5 average rating, 109 reviews

Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Indoor spacesKitchenGrill

4.88 out of 5 average rating, 108 reviews

A spacious living area features a modern sectional sofa adorned with various cushions, positioned around a round coffee table. Exposed wooden beams and high ceilings create an open atmosphere. A staircase leads to an upper level, and natural light illuminates the well-equipped kitchen visible in the background.

Home in Lee

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Indoor spacesKitchenCleanliness

Superhost

Home in Becket

Berkshires Lodge | Pool, Hot Tub & Fire Pit

KitchenIndoor spacesPets

4.86 out of 5 average rating, 118 reviews

4.9 out of 5 average rating, 101 reviews

Home in Sheffield

Berkshire Getaway~ No Pet Fee! Walk to Distillery

KitchenFamilyAccess

4.94 out of 5 average rating, 135 reviews

Home in Becket

HOT TUB! Dog & Family Friendly in the Berkshires!

Indoor spacesFamilyLayout

Family- and pet-friendly home rentals

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, 143 reviews

Never too early to book for the Holidays & NYE!

Indoor spacesKitchenGetting around

A two-story wooden house is nestled among lush greenery, featuring a balcony that overlooks the surrounding landscape. Vibrant trees, including a reddish-orange flowering tree, add color to the natural setting, creating a serene atmosphere.

4.89 out of 5 average rating, 102 reviews

Charming, view, large deck, private/walk downtown

Indoor spacesKitchenHiking

4.95 out of 5 average rating, 191 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!

FamilyIndoor spacesDecor

Superhost

The exterior of a two-story yellow house is presented, featuring a front porch with large windows and a central door. A water tower is visible in the background, surrounded by greenery and a gravel pathway leading to the entrance.

4.7 out of 5 average rating, 128 reviews

Relaxing Housatonic Retreat

KitchenIndoor spacesRiver

4.96 out of 5 average rating, 114 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 Near Hudson with Private Sauna

FamilyIndoor spacesSleep quality

Tiny home in New Marlborough

Bedroom Forest View I Sauna I Fire-pit I Trails

Indoor spacesKitchenQuiet

4.94 out of 5 average rating, 201 reviews

4.97 out of 5 average rating, 143 reviews

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

Home in Lee

Stylish Mid-century Modern Berkshires Cape

Indoor spacesFamilyNearby

4.95 out of 5 average rating, 320 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.

FamilyKitchenCondition

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 114 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.

Indoor spacesFamilyPool

4.93 out of 5 average rating, 106 reviews

A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.

Home in Lee

Berkshire Vacation Home in Lee

Indoor spacesKitchenTV

4.91 out of 5 average rating, 185 reviews

Home in Catskill

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

FamilyIndoor spacesCheck-in

4.98 out of 5 average rating, 178 reviews

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

Sackett & Van Dam Guest House @ Little 9 Farm 1706

KitchenFamilyQuiet

4.93 out of 5 average rating, 109 reviews

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

FamilyIndoor spacesTV

4.96 out of 5 average rating, 113 reviews

Home in Athens

Lake House close to Skiing & Indoor Hot Tub

KitchenFamilyBeach

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

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

Indoor spacesKitchenRiver

4.94 out of 5 average rating, 198 reviews