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
Home in Chester
4.96 out of 5 average rating, 315 reviewsRiverfront Getaway
Home in Northampton
4.88 out of 5 average rating, 572 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Cottage in Shaftsbury
4.99 out of 5 average rating, 606 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Bungalow in Easthampton
4.92 out of 5 average rating, 438 reviewsThe Creation Station
Home in Colebrook
4.99 out of 5 average rating, 204 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Home in Colrain
4.94 out of 5 average rating, 158 reviewsSecluded Farmhouse Retreat - stunning views
Home in Shaftsbury
4.94 out of 5 average rating, 125 reviewsConverted Vermont Barn on 6.5 acres with hot tub
Cabin in Monterey
4.95 out of 5 average rating, 252 reviewsAmazing Berkshire Mountains Cabin
Family- and pet-friendly home rentals
Home in Feeding Hills
4.89 out of 5 average rating, 891 reviewsFarm Fresh Feeding Hills
Apartment in Northampton
4.95 out of 5 average rating, 221 reviewsCedar Wet Room w Soaking Tub
Apartment in Northampton
4.96 out of 5 average rating, 267 reviewsRoost House (2 BR Apt. downtown)
Guest suite in Charlton
4.86 out of 5 average rating, 384 reviewsBaker Pond Hideaway
Farm stay in West Simsbury
4.95 out of 5 average rating, 438 reviewsFlamig Farm Staycation
Apartment in Ashfield
4.86 out of 5 average rating, 216 reviewsZachariah House Main St. Ashfield
Farm stay in Southbridge
4.89 out of 5 average rating, 297 reviewsScandanavian Wigwam with Sauna and Forest Baths
Loft in Northampton
4.97 out of 5 average rating, 255 reviewsLight-filled Studio Apt. Near Smith
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Apartment in Northampton
4.97 out of 5 average rating, 251 reviewsSunny Inspirit Apartment in best downtown location
Farm stay in Rutland
4.97 out of 5 average rating, 320 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
Apartment in Glastonbury
4.9 out of 5 average rating, 411 reviewsQuiet 2 bed room apt w/ private entrance.
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Woodstock
4.93 out of 5 average rating, 213 reviewsCedar Ridge
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- Family travel hub Tips and inspiration
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