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, 312 reviewsRiverfront Getaway
Dec 8 – 15
Home in Northampton
4.88 out of 5 average rating, 568 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Jul 1 – 8
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 26 – Aug 2
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Mar 20 – 27
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Feb 24 – Mar 3
Home in Colrain
4.94 out of 5 average rating, 156 reviewsSecluded Farmhouse Retreat - stunning views
Nov 8 – 15
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 26 – Sep 2
Guest suite in Mansfield
4.95 out of 5 average rating, 194 reviewsCozy private apt 8 mins from UCONN - solar powered
Jul 31 – Aug 7
Family- and pet-friendly home rentals
Apartment in Northampton
4.96 out of 5 average rating, 265 reviewsRoost House (2 BR Apt. downtown)
Jun 19 – 26
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Dec 17 – 24
Home in Feeding Hills
4.89 out of 5 average rating, 886 reviewsFarm Fresh Feeding Hills
Sep 16 – 23
Apartment in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
Aug 23 – 30
Loft in Northampton
4.97 out of 5 average rating, 252 reviewsLight-filled Studio Apt. Near Smith
Mar 15 – 22
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Nov 26 – Dec 3
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
Jan 16 – 23
Home in Russell
4.96 out of 5 average rating, 227 reviewsSouth Quarter House
Dec 11 – 18
Family-friendly home rentals with a pool
Apartment in Northampton
4.96 out of 5 average rating, 200 reviewsWood, sunshine & movies in best downtown location
Jun 9 – 16
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
Feb 20 – 27
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Dec 12 – 19
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Nov 10 – 17
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 31 – Sep 7
Home in Woodstock
4.93 out of 5 average rating, 209 reviewsCedar Ridge
Mar 23 – 30
Home in Litchfield
4.93 out of 5 average rating, 164 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 4 – 11
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Dec 1 – 8
Destinations to explore
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