
Family-friendly holiday rentals in Berkshire County
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Top-rated family-friendly rentals in Berkshire County
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Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

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. Approved pet = approved Pet Agreement.

Stylish Shales Brook Cottage-Cozy up to happiness
Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

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.

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.

HOT TUB! Berkshires: Dog & Family Friendly!
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 -Generator on site

Jaw dropping mountain & lake views
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

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.

Stylish Mid-century Modern Berkshires Cape
Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. 15 minutes from Butternut ski to south + Bousquet to the north, 35 min to Jiminy Peak. Cozy up by the wood burning fireplace and enjoy the winter wonderland! The house is decorated in mid century modern style with gorgeous design touches throughout!

Historic 1810 Farmhouse - Fully Renovated
Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!
Popular amenities for Berkshire County family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful House By The Lake W/Jetted Hot Tub

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

The Catamount Ski Haus with Pool & Hot Tub

Art House! W Hot Tub By Mass Moca

Berkshire family getaway at Jiminy Peak!

Spring Mountain Retreat + Views, Fire Pit & Tub

Lakeside 3-BR Berkshires Residence

Beautiful 2-BR + Loft w/ Hot Tub at Lake Ashmere
Family- and pet-friendly home rentals

Carriage house with Chef's Kitchen, close to town

A paradise in the woods, minutes from MASS MoCA

Private Home in The Berkshires (New Hot Tub!)

Enjoy every season the Berkshires have to offer.

Swiss Chalet Style Timberframe Home in Berkshires

Sweet Victorian in Housatonic

Winter retreat with scenic views in the Berkshires

Berkshires/Ski/Pet FriendlyTanglewood/PrivateRanch
Family-friendly home rentals with a pool

Friends & Family Retreat • Hot Tub • Heated Pool

Classic New England Home, Direct trail access

Berkshire Mountain House

Beautiful Jiminy Peak Townhome Family Friendly

Sweet Dreams Retreat

Stunning luxury home with pool

Hilltop: Panoramic Views w/ Pool near Catamount

Hollywood Bungalow in the Berkshires #C0191633410
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- Family-friendly rentals Massachusetts
- Family-friendly rentals United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Mount Snow Ski Resort
- Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- June Farms
- Ski Sundown
- Norman Rockwell Museum
- Naumkeag
- Opus 40
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery
- Hancock Shaker Village
- New York State Museum
- Poets' Walk Park
- Rensselaer Polytechnic Institute
- Things to do Berkshire County
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