
Family-friendly holiday rentals in Chesterfield
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chesterfield
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 Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Cabin
4.92 out of 5 average rating, 346 reviewsThe Rabbit Hole - Luxury Cabin in heart of Stowe

Guest suite
4.75 out of 5 average rating, 284 reviewsApartment, comfy and cozy with kitchen + hot tub

Home
4.96 out of 5 average rating, 228 reviewsThe Brookside @ Wilmington, NY

Home
4.94 out of 5 average rating, 186 reviewsHot tub, foosball, surrounded by nature!

Cabin
4.77 out of 5 average rating, 442 reviewsCanary Cabin

Chalet
4.92 out of 5 average rating, 178 reviewsKillington ski house winter MTbike -new jacuzzi

Home
4.96 out of 5 average rating, 129 reviewsPeaceful setting with Mountain Views

Cabin
5 out of 5 average rating, 103 reviews#7 - Hemlock Hideaway Cabin
Family- and pet-friendly home rentals

Home
4.99 out of 5 average rating, 296 reviewsCozy home Lake Placid Village

Home
4.82 out of 5 average rating, 171 reviewsFox Hollow on Sentinel

Home
4.88 out of 5 average rating, 161 reviewsBirchwood Lodge - Our Home in the Woods

Chalet
4.96 out of 5 average rating, 157 reviewsComfortable Mountain View Retreat

Home
4.96 out of 5 average rating, 145 reviewsPlacid Point-Walk Downtown

Home
4.95 out of 5 average rating, 192 reviewsThe McKinley House

Flat
4.9 out of 5 average rating, 345 reviewsWhiteface View Retreat STR # -200022

Home
4.83 out of 5 average rating, 464 reviewsThe Sanctuary: 3 Bedrooms, Easy Walking, +Parking!
Family-friendly home rentals with a pool

Apartment
4.79 out of 5 average rating, 135 reviewsLuxury 1 Bedroom at Topnotch Resort!

Guest house
5 out of 5 average rating, 210 reviewsChilson Brook Alpacas

Apartment
4.87 out of 5 average rating, 187 reviewsSki In/Ski Out with upgrades!

Home
4.88 out of 5 average rating, 255 reviewsLodge At Spruce Peak Alpine Studio Pool / Mt Views

Apartment
4.97 out of 5 average rating, 123 reviewsTWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO

Flat
4.77 out of 5 average rating, 111 reviewsTheatre in the Woods - Stowe, VT

Home
4.98 out of 5 average rating, 252 reviewsEPIC Stowe Getaway - Great For Families & Friends

Townhouse
4.85 out of 5 average rating, 123 reviewsSpacious 4 Bdrm Townhouse Between Town & Mountain
Destinations to explore
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