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
8–15 Nov
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Cottage in Shaftsbury
4.99 out of 5 average rating, 600 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
6–13 Mar
Home in Colrain
4.94 out of 5 average rating, 155 reviewsSecluded Farmhouse Retreat - stunning views
28 Dec – 4 Jan
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
7–14 Nov
Home in Shaftsbury
4.93 out of 5 average rating, 122 reviewsConverted Vermont Barn on 6.5 acres with hot tub
14–21 Nov
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
1–8 Aug
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
5–12 Aug
Family- and pet-friendly home rentals
Guest suite in Northampton
4.76 out of 5 average rating, 836 reviewsPrivate Guest House Downtown Noho
19–24 Jul
Guest suite in Charlemont
4.9 out of 5 average rating, 183 reviewsUnique People & Pet-Welcoming Haven
10–17 Mar
Home in Feeding Hills
4.89 out of 5 average rating, 885 reviewsFarm Fresh Feeding Hills
1–8 Sep
Flat in Ashfield
4.86 out of 5 average rating, 215 reviewsZachariah House Main St. Ashfield
21–28 Aug
Loft in Northampton
4.97 out of 5 average rating, 251 reviewsLight-filled Studio Apt. Near Smith
3–10 Nov
Farm stay in West Simsbury
4.95 out of 5 average rating, 432 reviewsFlamig Farm Staycation
27 Feb – 6 Mar
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
30 May – 6 Jun
Guest house in Stephentown
5.0 out of 5 average rating, 361 reviewsDog Friendly Studio
15–22 Nov
Family-friendly home rentals with a pool
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
11–18 Mar
Guest suite in Brooklyn
4.92 out of 5 average rating, 153 reviewsAffordable In-Law Apartment in Brooklyn, CT
20–27 Feb
Guest house in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
29 Aug – 5 Sep
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
10–17 Jan
Home in Woodstock
4.93 out of 5 average rating, 209 reviewsCedar Ridge
16–23 Apr
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
30 Jan – 6 Feb
Flat in Brooklyn
4.85 out of 5 average rating, 205 reviews5 Bedroom, 3.5 bath rural residence with 40' pool
7–14 Oct
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
28 Sep – 5 Oct
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