Family-friendly vacation rentals in The Berkshires
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in The Berkshires
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires family-friendly rentals
Family-friendly home rentals with a hot tub
Cabin in Saugerties
4.86 out of 5 average rating, 175 reviewsContainer Cabin in the Catskills (Field)
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Home in Highland
4.96 out of 5 average rating, 111 reviewsHouse in Highland: Secluded Retreat
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Home in Craryville
4.92 out of 5 average rating, 220 reviewsThe City Farmers Upstate. Farm house with hot tub
Cabin in Johnstown
4.9 out of 5 average rating, 321 reviewsMoose Cabin: Superior Quality Camp Garoga. HOT TUB
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Family- and pet-friendly home rentals
Cottage in Claverack
4.98 out of 5 average rating, 247 reviews‘Clavashack’ Country Cottage
Cottage in Craryville
4.91 out of 5 average rating, 483 reviewsColumbia County Getaway - Raspberry Ridge Cottage
Guesthouse in Canaan
4.93 out of 5 average rating, 166 reviewsAiry cottage with meadow views in The Berkshires
Farm stay in West Simsbury
4.95 out of 5 average rating, 437 reviewsFlamig Farm Staycation
Farm stay in High Falls
4.87 out of 5 average rating, 813 reviewsDave's Milk Barn
Yurt in Pattersonville
4.99 out of 5 average rating, 784 reviewsMariaville Goat Farm Yurt
Cottage in Red Hook
4.98 out of 5 average rating, 600 reviewsbright serene + spacious barn
Home in New Paltz
4.97 out of 5 average rating, 681 reviewsVictorian Haven
Family-friendly home rentals with a pool
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Cabin in Saugerties
4.99 out of 5 average rating, 123 reviewsLovely cabin by the stream
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in New Paltz
4.98 out of 5 average rating, 439 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Destinations to explore
- Family-friendly rentals United States
- Family-friendly rentals Long Island
- Family-friendly rentals New York
- Rentals with a fire pit The Berkshires
- Guesthouse rentals The Berkshires
- Ski-in/ski-out rentals The Berkshires
- Rentals with a fireplace The Berkshires
- Rentals with a home theater The Berkshires
- Cottage rentals The Berkshires
- Townhouse rentals The Berkshires
- Kid-friendly rentals The Berkshires
- Rentals with a patio The Berkshires
- Rentals with a kayak The Berkshires
- Rentals with an EV charger The Berkshires
- Rentals with a hot tub The Berkshires
- Monthly Rentals The Berkshires
- Boutique hotel rentals The Berkshires
- Fitness-friendly rentals The Berkshires
- Lakehouse rentals The Berkshires
- Wheelchair accessible rentals The Berkshires
- Rentals with breakfast The Berkshires
- Pet-friendly rentals The Berkshires
- Rentals with pools The Berkshires
- House rentals The Berkshires
- Farmstay rentals The Berkshires
- Private suite rentals The Berkshires
- Beachfront rentals The Berkshires
- Luxury rentals The Berkshires
- Chalet rentals The Berkshires
- Condo rentals The Berkshires
- Apartment rentals The Berkshires
- Hotel rentals The Berkshires
- Rentals with beach access The Berkshires
- Cabin rentals The Berkshires
- Rentals with an accessible height toilet The Berkshires
- Smoking-friendly rentals The Berkshires
- Rentals with a washer and dryer The Berkshires
- Waterfront rentals The Berkshires
- Aparthotel rentals The Berkshires
- Rentals with outdoor seating The Berkshires
- Rentals with a sauna The Berkshires
- Bed and breakfasts The Berkshires
- Rentals with lake access The Berkshires
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- 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
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- 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
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom