Kid-friendly holiday rentals in The Berkshires
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in The Berkshires
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires family-friendly rentals
Kid-friendly house rentals
Home
4.93 out of 5 average rating, 171 reviewsTranquil Tree-House on the beautiful Hudson River
Home
4.93 out of 5 average rating, 137 reviewsLake front retreat - Stylish Berkshire home
Home
4.9 out of 5 average rating, 226 reviews1817 Berkshire Farmhouse- Close to Everything.
Home
4.97 out of 5 average rating, 104 reviewsDirect Lakefront Home on Otis Reservoir Giant Yard
Home
4.87 out of 5 average rating, 323 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home
4.97 out of 5 average rating, 318 reviewsThis New House
Home
4.92 out of 5 average rating, 251 reviewsSecluded modern forest cabin with private brook
Home
4.99 out of 5 average rating, 104 reviewsModern House with Mountain View @Getawind
Family-friendly apartment rentals
Rental unit
4.88 out of 5 average rating, 187 reviewsStation House 1E Private Room & Bath
Rental unit
4.97 out of 5 average rating, 259 reviewsSunny, light filled loft in 1873 Colonial
Rental unit
4.94 out of 5 average rating, 325 reviewsBike Path Hideaway Near Smith, Cooley, Northampton
Rental unit
4.92 out of 5 average rating, 139 reviewsPrivate Berkshire Barn Apartment
Rental unit
4.87 out of 5 average rating, 171 reviewsThe Beer Diviner Brewery Apartment
Rental unit
4.95 out of 5 average rating, 262 reviewsSunny carriage house apartment
Rental unit
5 out of 5 average rating, 273 reviewsMountain View Retreat~Sunny Hill Golf / Skiing
Rental unit
4.91 out of 5 average rating, 369 reviewsGateway to the Berkshires
Family-friendly apartment rentals
Apartment
4.88 out of 5 average rating, 165 reviewsCozy Mountain hideaway Windham, Hunter
Apartment
4.96 out of 5 average rating, 133 reviewsEntire place to yourself Cromwell/Middletown Line
Apartment
4.89 out of 5 average rating, 219 reviewsElegant, spacious studio apt in historic mansion
Apartment
4.97 out of 5 average rating, 595 reviewsSki on/ Ski off Stylish Condo Hunter Mountain
Apartment
4.99 out of 5 average rating, 537 reviewsRustic Spa Retreat
Apartment
4.93 out of 5 average rating, 325 reviewsPrivate & Quiet Studio Apt. in Vermont
Apartment
4.84 out of 5 average rating, 141 reviewsCozy Condo @ Jiminy Peak
Apartment
4.97 out of 5 average rating, 462 reviews*Great Reviews* Hunter Mtn. Cozy Clean Close Condo
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals New York
- Family-friendly rentals Long Island
- Rentals with a hot tub The Berkshires
- Rentals with pools The Berkshires
- Lakehouse rentals The Berkshires
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- Farm stay rentals The Berkshires
- Holiday home rentals The Berkshires
- Pet-friendly rentals The Berkshires
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- Monthly Rentals The Berkshires
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- Rentals with a cinema The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
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- Rentals with an accessible-height toilet The Berkshires
- Townhouse rentals The Berkshires
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- House rentals The Berkshires
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- Rentals with breakfast The Berkshires
- Family-friendly rentals The Berkshires
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- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
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- Luxury Cabins United States
- Holiday Chalets United Kingdom
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- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
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- Beach Houses United Kingdom
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
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- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom