A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Family friendly Hotels in Chester, New York

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Check availability on Chester Family friendly Hotels

This weekend
Jul 3 - Jul 5
Next weekend
Jul 10 - Jul 12

Our top choices for Chester family-friendly hotels

Exterior

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
The price is P13,153
P14,879 total
includes taxes & fees
Jul 2 - Jul 3
The Dominion House Bed & Breakfast
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (64 reviews)
The price is P6,706
P8,257 total
includes taxes & fees
Jul 22 - Jul 23
Comfort Suites Central Valley - Woodbury
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (169 reviews)
The price is P6,648
P7,747 total
includes taxes & fees
Jul 2 - Jul 3
Borland House Inn
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,004 reviews)
  • cleanliness
    Engaging hotel with mountain adventures for kids offers free breakfast and nearby waterpark thrills for all ages.
The price is P6,250
P7,164 total
includes taxes & fees
Jul 26 - Jul 27
Quality Inn near Mountain Creek
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    Splash into family-friendly fun at this stylish hotel with an indoor pool, on-site bistro, and prime location near LEGOLAND® New York.
The price is P7,228
P8,538 total
includes taxes & fees
Jul 19 - Jul 20
Courtyard by Marriott Middletown Goshen
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Family fun at Hampton Inn by Hilton Middletown starts with a seasonal pool and LEGOLAND® just a short drive away.
The price is P6,945
P8,203 total
includes taxes & fees
Jul 19 - Jul 20
Hampton Inn by Hilton Middletown
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very Good, (148 reviews)
The price is P5,668
P6,553 total
includes taxes & fees
Jul 15 - Jul 16
Spark by Hilton Fishkill
Lobby

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point
2.0 star property
Newburgh
4.8 out of 10, (1,001 reviews)
  • cleanliness
    Family paradise with workout facilities awaits near Algonquin Park—a complimentary adventure with modern comforts.
The price is P4,405
P5,203 total
includes taxes & fees
Jul 6 - Jul 7
Ramada by Wyndham Newburgh/West Point
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"The hotel was updated and clean and perfect to accompany a small dog. They can have more electric chargers."
Changshik 2-night trip
Posted 1 hour ago
Crowne Plaza Suffern - Mahwah by IHG

Frequently asked questions

What's Chester like for family-friendly vacations?
The welcoming destination of Chester is a great choice if you've been considering a vacation with the kids. The excursions, swimming spots, and coffee shops are just some of the things that make this an attractive family vacation spot. Take to the air and fly into Stewart Intl. Airport (SWF), which is located 13.5 mi (21.7 km) from the city center.
What's the best place to stay for a family vacation in Chester?
The Dominion House Bed & Breakfast is a B&B with an outdoor pool and free parking, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Chester?
The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Chester are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.
What's there to see and do with your family in Chester?
While you are visiting Chester, you and the family might want to check out some interesting spots such as Sugar Loaf Performing Arts Center, LEGOLAND® New York, and Monroe Federal Plaza Shopping Center. Make sure you have lots of time for activities like Galleria at Crystal Run and Mount Peter Ski Area.

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