
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

Private Apt. on Farm, Hot Tub with views!

Top of the World! Jacuzzi! Private Hiking Trails!

Okemo Ski Chalet with Hot Tub

Stunning Rustic Apple Barn - hot tub & sauna

Ski Chalet with Hot Tub on Okemo Mountain

Vermont Getaway Apartment

Spacious Renovated Barn Apt on 100 acres!

Rustic and Cozy Vermont Getaway at Sugarwood Cabin
Family- and pet-friendly home rentals

Cowshed Cabin Farm

Pinecone Pond

Moon Valley Country Retreat no clean fee pets yes

Historic 1832 Parker House ~ Sleeps 10, Pool Table

The Carriage Barn

Ephriam Bruce House- ON RIVER IN VILLAGE CENTER

Apple Blossom Cottage: A Tiny House

Yurt In The Woods - Private Refuge
Family-friendly home rentals with a pool

Magical Farm Getaway - a must visit!

Bear's Den - Mt Snow Townhome w/ Heated Pool!

Cozy, spacious, 3 bedrooms, 4 beds, swimming pool.

One Bedroom Suite Near Okemo

Serene Top Floor Condo (resort style amenities)

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Hike bike golf 1 bedroom 1 nght Ok Aug is open

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!
Quick stats about vacation rentals that are family-friendly in Chester
Total rentals
60 properties
Nightly prices starting at
R1,250 ZAR before taxes and fees
Total number of reviews
2.8K reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
Destinations to explore
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- Rentals with a washer and dryer Chester
- Rentals with a patio Chester
- Pet-friendly rentals Chester
- House rentals Chester
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- Rentals with outdoor seating Chester
- Rentals with a fire pit Chester
- Rentals with a fireplace Chester
- Family-friendly rentals Windsor County
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Dorset Field Club
- Stratton Mountain Resort
- Ragged Mountain Resort
- Bretwood Golf Course
- Hildene, The Lincoln Family Home
- Autumn Mountain Winery
- Bromley Mountain Ski Resort
- Clarksburg State Park
- Baker Hill Golf Club
- Fox Run Golf Club
- Mount Sunapee Resort
- Veterans Memorial Recreation Area Ski Hill
- Crotched Mountain Ski and Ride
- Hooper Golf Course