Family-friendly holiday 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.
Holiday 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
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Apartment in Killington
4.77 out of 5 average rating, 283 reviewsSerene Killington Condo (resort style amenities)
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Cottage in Shaftsbury
4.99 out of 5 average rating, 601 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Loft in Ludlow
4.95 out of 5 average rating, 736 reviewsSpacious Renovated Barn Apt on 100 acres!
Home in Lempster
4.88 out of 5 average rating, 368 reviewsDreamy lakefront cottage with views to die for!
Home in Newfane
4.97 out of 5 average rating, 115 reviewsPeaceful cabin close to skiing & Brattleboro
Home in Ludlow
4.93 out of 5 average rating, 138 reviewsOKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!
Family- and pet-friendly home rentals
Cottage in Jamaica
4.82 out of 5 average rating, 466 reviewsForest Cottage-Swim-Views-FirePit-7min to Stratton
Home in Weston
4.95 out of 5 average rating, 228 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Flat in Town of Rockingham
4.81 out of 5 average rating, 162 reviewsApartment on Main Street
Flat in Newfane
4.97 out of 5 average rating, 406 reviewsRock River Retreat: Pets Welcome
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
Cabin in Brattleboro
4.89 out of 5 average rating, 444 reviewsCottage
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
Flat in Ludlow
4.92 out of 5 average rating, 255 reviewsOkemo Vermont Getaway
Family-friendly home rentals with a pool
Apartment in Killington
4.92 out of 5 average rating, 392 reviewsApril open 1 bedroom 1 night Ok Free shuttle
Apartment in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Apartment in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Apartment in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
Quick stats about holiday rentals that are family-friendly in Chester
Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Total number of reviews
2.3T reviews
Nightly prices starting at
₹5,843 before taxes and fees
Destinations to explore
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