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
Nov 7 – 14
Home in Northampton
4.88 out of 5 average rating, 568 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Jul 1 – 8
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
Mar 29 – Apr 5
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 2 – 9
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
Aug 6 – 13
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
Nov 14 – 21
Guest suite in Mansfield
4.95 out of 5 average rating, 194 reviewsCozy private apt 8 mins from UCONN - solar powered
Oct 6 – 13
Home in Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Apr 13 – 20
Family- and pet-friendly home rentals
Guest suite in Northampton
4.76 out of 5 average rating, 837 reviewsPrivate Guest House Downtown Noho
Jul 20 – 25
Cottage in Bernardston
4.88 out of 5 average rating, 287 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
Jan 20 – 27
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
Apr 20 – 27
Home in Feeding Hills
4.89 out of 5 average rating, 886 reviewsFarm Fresh Feeding Hills
Oct 17 – 24
Apartment in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
Aug 22 – 29
Farm stay in West Simsbury
4.95 out of 5 average rating, 434 reviewsFlamig Farm Staycation
Feb 20 – 27
Loft in Northampton
4.97 out of 5 average rating, 251 reviewsLight-filled Studio Apt. Near Smith
Dec 27 – Jan 3
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
Sep 9 – 16
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
Aug 17 – 24
Bungalow in Easthampton
4.92 out of 5 average rating, 433 reviewsThe Creation Station
Jul 26 – Aug 2
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 30 – Sep 6
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Oct 8 – 15
Home in Woodstock
4.93 out of 5 average rating, 209 reviewsCedar Ridge
Feb 17 – 24
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Jun 5 – 12
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Sep 5 – 12
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Jan 31 – Feb 7
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- Family travel hub Tips and inspiration
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