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
Cottage in Shaftsbury
4.99 out of 5 average rating, 599 reviewsVermont Schoolhouse Farm Cottage - Sauna + Hot Tub
Apr 13 – 20
Cabin in Londonderry
4.82 out of 5 average rating, 421 reviewsThe Honeymoon Barn - hot tub/sauna #1 Airbb S. VT
Apr 20 – 27
Loft in Ludlow
4.95 out of 5 average rating, 735 reviewsSpacious Renovated Barn Apt on 100 acres!
Oct 9 – 16
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Jul 12 – 19
Home in Lempster
4.88 out of 5 average rating, 367 reviewsDreamy lakefront cottage with views to die for!
Feb 10 – 15
Home in Newfane
4.97 out of 5 average rating, 114 reviewsPeaceful cabin close to skiing & Brattleboro
Jan 9 – 16
Home in Ludlow
4.93 out of 5 average rating, 138 reviewsOKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!
Nov 4 – 11
Condo in Killington
4.77 out of 5 average rating, 282 reviewsSerene Killington Condo (resort style amenities)
Aug 13 – 20
Family- and pet-friendly home rentals
Apartment in Town of Rockingham
4.82 out of 5 average rating, 159 reviewsApartment on Main Street
Oct 8 – 15
Cottage in Jamaica
4.82 out of 5 average rating, 464 reviewsForest Cottage ~ 7min to Stratton, Private, Views
Jul 19 – 26
Guesthouse in Granville
4.9 out of 5 average rating, 785 reviewsMoon Valley Country Retreat no clean fee pets yes
Dec 20 – 27
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Sep 13 – 20
Apartment in Ludlow
4.92 out of 5 average rating, 255 reviewsOkemo Vermont Getaway
Apr 2 – 9
Home in Grafton
4.97 out of 5 average rating, 130 reviewsEphriam Bruce House- ON RIVER IN VILLAGE CENTER
Sep 16 – 23
Cabin in Brattleboro
4.89 out of 5 average rating, 442 reviewsCottage
Jul 12 – 19
Home in Town of Rockingham
4.89 out of 5 average rating, 113 reviewsBeautiful Home in the Mountains - The Fox & Owl
Jul 12 – 19
Family-friendly home rentals with a pool
Guesthouse in Williamstown
4.93 out of 5 average rating, 219 reviewsPerfect Base for Your Berkshire Adventure
Aug 2 – 9
Condo in Killington
4.92 out of 5 average rating, 392 reviewsApril open 1 bedroom 1 night Ok Free shuttle
Sep 19 – 26
Bungalow in Williamstown
4.89 out of 5 average rating, 202 reviewsHollywood Bungalow in the Berkshires
Apr 18 – 25
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Jan 12 – 19
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Aug 19 – 26
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Apr 12 – 19
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Feb 10 – 17
Condo in Killington
4.82 out of 5 average rating, 250 reviewsSki, Ride, Walk On/Off Condo On Pico at Killington
Apr 11 – 18
Quick stats about vacation 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
2.3K reviews
Nightly prices starting at
G$14,636 GYD before taxes and fees
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