Family-friendly vacation rentals in Berkshire County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Berkshire County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Berkshire County family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Lenox
4.73 out of 5 average rating, 74 reviewsLuxury Fox Hollow Home-Laurel Lake
Chalet in Richmond
4.97 out of 5 average rating, 93 reviewsUpdated Berkshires Chalet Mins to Tanglewood/Lenox
Home in Pittsfield
4.81 out of 5 average rating, 171 reviewsBeautiful House By The Lake W/Jetted Hot Tub
Home in East Chatham
4.79 out of 5 average rating, 184 reviewsHot tub in Berkshires! 3 Queen 2 Bath! Windswept!
Home in Lee
4.96 out of 5 average rating, 77 reviewsSpectacular Berkshire Retreat on Private Lake
Cabin in Becket
5 out of 5 average rating, 265 reviewsWaldtreff - quiet grand cabin
Home in Lanesboro
4.95 out of 5 average rating, 19 reviewsMy Mountain Haven- The Perfect Escape
Family- and pet-friendly home rentals
Home in Lanesborough
4.9 out of 5 average rating, 108 reviewsElmwood Farmhouse
Farm stay in New Ashford
4.89 out of 5 average rating, 238 reviewsSheep Barn on the Greylock Valley Estate
Home in Otis
4.94 out of 5 average rating, 142 reviewsBerkshires hideaway! Hikes & serenity near lake
Home in Williamstown
4.82 out of 5 average rating, 186 reviewsWalking distance to downtown
Rental unit in Great Barrington
4.93 out of 5 average rating, 190 reviewsSecluded but not isolated Berkshire Retreat
Cottage in East Chatham
4.93 out of 5 average rating, 202 reviewsBeautifully Nestled Berkshires Home
Cabin in Hillsdale
4.8 out of 5 average rating, 312 reviewsRustic, peaceful and affordable cabin
Cabin in Lee
4.91 out of 5 average rating, 117 reviewsFall Break discount at The Beaver Dam!
Family-friendly home rentals with a pool
Rental unit in Lee
4.92 out of 5 average rating, 25 reviewsDream Vacation
Home in Hancock
4.86 out of 5 average rating, 44 reviewsJiminy Peak Peaceful Home in Berkshires
Home in Great Barrington
4.88 out of 5 average rating, 17 reviewsFun Farmhouse
Home in Canaan
4.99 out of 5 average rating, 83 reviewsBerkshire Lake House, gunite pool, Chef's Kitchen
Hotel room in Hancock
4.83 out of 5 average rating, 12 reviewsWyndham Bentley Brook ** 2BR Deluxe
Condo in Hancock
4.84 out of 5 average rating, 141 reviewsCozy Condo @ Jiminy Peak
Chalet in Monterey
5 out of 5 average rating, 10 reviewsStunning Log Cabin with brand new Pickleball court
Home in Canaan
4.67 out of 5 average rating, 63 reviewsR3Bliss - Estate with Hot Tub, Tennis Court & Pool
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