Family-friendly vacation rentals in Pioneer Valley
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Pioneer Valley
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 Pioneer Valley family-friendly rentals
Family-friendly home rentals with a hot tub
Bungalow in Easthampton
4.92 out of 5 average rating, 436 reviewsThe Creation Station
Home in Chester
4.96 out of 5 average rating, 313 reviewsRiverfront Getaway
Home in Northampton
4.88 out of 5 average rating, 569 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Cottage in Shaftsbury
4.99 out of 5 average rating, 605 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Home in Colrain
4.94 out of 5 average rating, 156 reviewsSecluded Farmhouse Retreat - stunning views
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 Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Family- and pet-friendly home rentals
Apartment in Northampton
4.95 out of 5 average rating, 220 reviewsCedar Wet Room w Soaking Tub
Apartment in Northampton
4.96 out of 5 average rating, 266 reviewsRoost House (2 BR Apt. downtown)
Home in Feeding Hills
4.89 out of 5 average rating, 887 reviewsFarm Fresh Feeding Hills
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Loft in Northampton
4.97 out of 5 average rating, 253 reviewsLight-filled Studio Apt. Near Smith
Apartment in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
Farm stay in West Simsbury
4.95 out of 5 average rating, 436 reviewsFlamig Farm Staycation
Farm stay in Southbridge
4.89 out of 5 average rating, 296 reviewsScandanavian Wigwam with Sauna and Forest Baths
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Home in Woodstock
4.93 out of 5 average rating, 210 reviewsCedar Ridge
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
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- Family travel hub Tips and inspiration
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