
Family-friendly holiday rentals in Great Barrington
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Great Barrington
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Walk Everywhere! | Relax in Easy Elegance!
Gracious in-town apartment feels like home: living room, dining room, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Quick walk to shops, restaurants, theaters, farmers’ market, and a short drive to arts offerings, hiking, skiing, swimming. Or treat yourself to a spa day at a local wellness center. Spectrum WiFi. Please note, there is no TV. Bedrooms are small but there’s plenty of space to spread out, relax, read or play games in the spacious apartment or on the shared porch.

King Bed|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

Best of the Berkshires + Hot Tub by Evergreen Home
Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

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.

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.

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.

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.

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.

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.

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.

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.

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.
Popular amenities for Great Barrington family-friendly rentals
Family-friendly home rentals with a hot tub

40-Foot Container Cabin in the Catskills

Relaxing secluded stay with loving social animals.

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

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Modern Cabin in the Woods with Hot Tub

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Luxury Prvt Estate w/Hot Tub+Gameroom nr Rhinebeck

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Family- and pet-friendly home rentals

Luxury Barn Retreat — All-Season Escape Awaits!

Berkshires Cottage by Lake. Year Round Adventures.

Private Berkshire Barn Apartment

Susie's Climax Creations

Lake House in the Berkshire (Access Dock & Canoe

The Copake Cabin - A rustic-modern retreat.

The Ancram A - Luxury Mid-Century Modern Cabin

Secluded but not isolated Berkshire Retreat
Family-friendly home rentals with a pool

Enchanting Upstate Cabin w Pool, Firepit

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Cozy cottage with pool, walking distance to lake

MODERN FARMHOUSE in the WOODS

Modern Upstate Cabin, near Rhinebeck NY

Le Soleil Suite - Pool, Mtn Views Near Hudson
When is the best time to visit Great Barrington?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $487 AUD | $472 AUD | $466 AUD | $459 AUD | $487 AUD | $536 AUD | $571 AUD | $547 AUD | $486 AUD | $486 AUD | $495 AUD | $550 AUD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Quick stats about holiday rentals that are family-friendly in Great Barrington

Total holiday rentals
Explore 160 holiday rentals in Great Barrington

Nightly prices starting at
Great Barrington holiday rentals start at $42 AUD per night before taxes and fees

Verified guest reviews
Over 7,320 verified reviews to help you choose

Pet-friendly accommodation
Find 80 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
100 properties have a dedicated workspace

Wi-Fi availability
160 of Great Barrington holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Great Barrington rentals

4.9 Average rating
Great Barrington stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with outdoor seating Great Barrington
- Cabin rentals Great Barrington
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- Rentals with a hot tub Great Barrington
- Rentals with a kayak Great Barrington
- Rentals with a washing machine and dryer Great Barrington
- Rentals with a fireplace Great Barrington
- House rentals Great Barrington
- Fitness-friendly rentals Great Barrington
- Rentals with lake access Great Barrington
- Pet-friendly rentals Great Barrington
- Rentals with pools Great Barrington
- Rentals with a fire pit Great Barrington
- Apartment rentals Great Barrington
- Rentals with a patio Great Barrington
- Family-friendly rentals Berkshire County
- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Taconic State Park
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- June Farms
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Opus 40
- Berkshire Botanical Garden
- Walkway Over the Hudson State Historic Park




