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
Jan 25 – Feb 1
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
Jul 10 – 17
Condo in Killington
4.77 out of 5 average rating, 282 reviewsSerene Killington Condo (resort style amenities)
Jul 4 – 11
Home in Lempster
4.88 out of 5 average rating, 367 reviewsDreamy lakefront cottage with views to die for!
Apr 11 – 16
Condo in Ludlow
4.8 out of 5 average rating, 148 reviewsEnjoy a Ski-On/Ski-Off Okemo Ski Getaway
Apr 6 – 13
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!
Aug 23 – 30
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
Oct 24 – 31
Home in Weston
4.95 out of 5 average rating, 227 reviewsReillys Rest -GreenMtns! Secluded-Pet-Kid friendly
Sep 13 – 20
Chalet in Dover
4.93 out of 5 average rating, 265 reviewsA charming VT chalet
Sep 18 – 25
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
Aug 5 – 12
Cottage in Dover
4.95 out of 5 average rating, 216 reviewsCozy summer cottage in the woods of southern VT
Jul 19 – 26
Family-friendly home rentals with a pool
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
Dec 4 – 11
Condo in Killington
4.97 out of 5 average rating, 116 reviews#45 Mountain Ski & Summer Condo with Private Sauna
Oct 4 – 11
Home in Salem
4.98 out of 5 average rating, 180 reviewsMagical Farm Getaway - a must visit!
Feb 21 – 28
Home in Wilmington
4.83 out of 5 average rating, 155 reviewsThe Vermont Barn (Mount Snow)
Feb 10 – 17
Guest suite in Killington
4.95 out of 5 average rating, 139 reviewsCozy, private, spacious, 3 bedrooms, 5 mi to K Rd.
May 10 – 17
Condo in Killington
4.9 out of 5 average rating, 232 reviewsA Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532
Dec 26 – Jan 2
Townhouse in Dover
4.96 out of 5 average rating, 136 reviewsBear's Den - Mt Snow Townhome w/ Ski Home Trail!
Nov 13 – 20
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
€ 65 before taxes and fees
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