
Family-friendly holiday 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.
Holiday 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

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Relaxing secluded stay with loving social animals.

Beautiful Timber Frame Retreat

Hilltown Cabin Hideaway: A River Runs Through It!

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Cozy Getaway | Pet Friendly | Litchfield Cty

Lake View, Hot Tub, 4 Kayaks, Central AC, Fire Pit

Norbrook Farm ~ Rustic farmhouse w/ pond & trails
Family- and pet-friendly home rentals
Woodstock Historic Artist Estate - The Pond House

Modern Upstate Cabin, near Rhinebeck NY

Modern Copake Falls Getaway - 8 Mins to Catamount

Swiss Chalet Style Timberframe Home in Berkshires

Enjoy every season the Berkshires have to offer.

Kitchenette|King Bed|Couch

Cozy Riverside Tiny House & Wood Sauna

Secluded Berkshire cabin with scenic views
Family-friendly home rentals with a pool

Plunge Pool, Sauna, AC! Modern Mountain Escape

midcentury mod * HOT TUB * walk out trail 2 mohonk

Kapitan’s Cottage: Private Retreat with Salt Pool

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Modern Barn on 12 acres w Sauna, FirePit+swimming

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Le Soleil Suite - Fire pit, Views 10 Min To Hudson

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Destinations to explore
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- Family-friendly rentals United States