Family-friendly vacation rentals in Chester
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chester
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 Chester family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Plymouth
4.95 out of 5 average rating, 237 reviewsTop of the World! Jacuzzi! Private Hiking Trails!
Chalet in Ludlow
4.95 out of 5 average rating, 118 reviewsOkemo Ski Chalet with Hot Tub
Home in Cavendish
4.84 out of 5 average rating, 141 reviewsOkemo-Ludlow, fireplace, hottub, sleeps 13
Condo in Killington
4.78 out of 5 average rating, 287 reviewsSerene Top Floor Condo (resort style amenities)
Chalet in Killington
4.87 out of 5 average rating, 242 reviewsLarge Chalet; Sauna, Hot Tub; Walk to Trail
Home in Newfane
4.98 out of 5 average rating, 130 reviewsPeaceful cabin close to skiing & Brattleboro
Home in Ludlow
4.97 out of 5 average rating, 151 reviewsSki Chalet with Hot Tub on Okemo Mountain
Loft in Ludlow
4.95 out of 5 average rating, 774 reviewsSpacious Renovated Barn Apt on 100 acres!
Family- and pet-friendly home rentals
Rental unit in Springfield
4.95 out of 5 average rating, 151 reviewsConnecticut River Odyssey
Cabin in Jamaica
4.89 out of 5 average rating, 370 reviewsForest Cabin-Swim-Views-Fire Pit-7 min to Stratton
Home in Danby
4.96 out of 5 average rating, 215 reviewsComfortable farmhouse with stunning views
Chalet in Dover
4.92 out of 5 average rating, 288 reviewsA charming VT chalet
Tiny home in Jamaica
4.94 out of 5 average rating, 1,214 reviewsApple Blossom Cottage: A Tiny House
Rental unit in Newfane
4.97 out of 5 average rating, 433 reviewsRock River Retreat: VT Oasis Pet Friendly
Home in Rochester
4.97 out of 5 average rating, 197 reviewsThe Guest House at Sky Hollow
Cabin in Pawlet
4.93 out of 5 average rating, 138 reviewsHickory Ridge, Vermont Log Cabin, no cleaning fee
Family-friendly home rentals with a pool
Guesthouse in Ticonderoga
5 out of 5 average rating, 210 reviewsChilson Brook Alpacas
Home in Salem
4.98 out of 5 average rating, 185 reviewsMagical Farm Getaway - a must visit!
Townhouse in Dover
4.96 out of 5 average rating, 143 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Condo in Killington
4.82 out of 5 average rating, 251 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Condo in Killington
4.96 out of 5 average rating, 128 reviews#45 Luxury Ski & Summer Condo with Private Sauna
Condo in Killington
4.93 out of 5 average rating, 415 reviewsPICO open Turkey week 1 bedroom 1 nite Ok shuttle
Condo in Killington
4.86 out of 5 average rating, 112 reviewsMountain Retreat: 4 Bdrm/2 Bath, Ski In, Bus Out
Quick stats about vacation rentals that are family-friendly in Chester
Total rentals
70 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
2.6K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
70 properties include access to wifi
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