Family-friendly holiday 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.
Holiday 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
14–21 Oct
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
25 Oct – 1 Nov
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
28 Oct – 4 Nov
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
24–31 Dec
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
14–21 Nov
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
9–16 Oct
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
24–31 Jan
Family- and pet-friendly home rentals
Guest suite in Northampton
4.76 out of 5 average rating, 836 reviewsPrivate Guest House Downtown Noho
23–28 Jul
Cottage in Bernardston
4.88 out of 5 average rating, 287 reviewsCozy, Quiet Cottage on Country rd 2 mil from I-91
29 Mar – 5 Apr
Flat in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
18–25 Aug
Home in Feeding Hills
4.89 out of 5 average rating, 885 reviewsFarm Fresh Feeding Hills
8–15 Aug
Loft in Northampton
4.97 out of 5 average rating, 251 reviewsLight-filled Studio Apt. Near Smith
12–19 Mar
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
14–21 Jun
Farm stay in West Simsbury
4.95 out of 5 average rating, 432 reviewsFlamig Farm Staycation
13–20 Mar
Flat in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
20–27 Nov
Family-friendly home rentals with a pool
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
21–28 Jul
Flat in Northampton
4.96 out of 5 average rating, 200 reviewsWood, sunshine & movies in best downtown location
2–9 Aug
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
15–22 Jun
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
5–12 Dec
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
19–26 Mar
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
17–24 Nov
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
27 Jan – 3 Feb
Barn in Pownal
4.94 out of 5 average rating, 78 reviewsArtist Bunkhouse Southern Vermont
2–9 Jun
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