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, 430 reviewsThe Creation Station
Jul 21 – 26
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Jul 30 – Aug 6
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep 8 – 15
Cottage in Shaftsbury
4.99 out of 5 average rating, 598 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Apr 13 – 20
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
Feb 25 – Mar 4
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Apr 1 – 8
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 20 – 27
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
Jun 5 – 12
Family- and pet-friendly home rentals
Cottage in Bernardston
4.88 out of 5 average rating, 286 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Mar 25 – Apr 1
Apartment in Northampton
4.96 out of 5 average rating, 264 reviewsRoost House (2 BR Apt. downtown)
Jul 10 – 17
Apartment in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
Jul 13 – 20
Home in Feeding Hills
4.89 out of 5 average rating, 884 reviewsFarm Fresh Feeding Hills
Sep 8 – 15
Loft in Northampton
4.98 out of 5 average rating, 250 reviewsLight-filled Studio Apt. Near Smith
Jul 27 – Aug 3
Farm stay in Southbridge
4.89 out of 5 average rating, 292 reviewsScandanavian Wigwam with Sauna and Forest Baths
Jun 11 – 16
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
Jul 19 – 26
Farm stay in West Simsbury
4.95 out of 5 average rating, 430 reviewsFlamig Farm Staycation
Mar 20 – 27
Family-friendly home rentals with a pool
Farm stay in Rutland
4.97 out of 5 average rating, 317 reviewsFarm Living
Dec 27 – Jan 3
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
Sep 8 – 15
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Sep 8 – 15
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Dec 4 – 11
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
May 28 – Jun 4
Home in Woodstock
4.93 out of 5 average rating, 207 reviewsCedar Ridge
Mar 24 – 31
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Feb 10 – 17
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