Family friendly Hotels in Chester, New York

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Check availability on Chester Family friendly Hotels

Our top choices for Chester family-friendly hotels

Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (163 reviews)
The price is P6,316
P7,358 total
includes taxes & fees
May 27 - May 28
Borland House Inn
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (42 reviews)
The price is P6,324
P7,787 total
includes taxes & fees
May 28 - May 29
Comfort Suites Central Valley - Woodbury
Exterior

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,005 reviews)
  • cleanliness
    Family fun awaits at this hotel with splashdown beach just minutes away and a convenient full-size breakfast each day.
The price is P6,372
P7,367 total
includes taxes & fees
May 27 - May 28
Quality Inn & Suites Fishkill South near I-84
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very Good, (88 reviews)
The price is P5,719
P6,612 total
includes taxes & fees
Jun 3 - Jun 4
Spark by Hilton Fishkill
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,011 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 P7,030
P8,304 total
includes taxes & fees
Jun 10 - Jun 11
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, (1,001 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 P6,464
P7,635 total
includes taxes & fees
Jun 2 - Jun 3
Hampton Inn by Hilton Middletown
Seasonal outdoor pool, pool umbrellas, sun loungers

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (41 reviews)
  • cleanliness
    Splash into family adventure at LEGOLAND Hotel with an outdoor pool, playground, and game room full of toys for endless fun.
The price is P18,618
P29,483 total
includes taxes & fees
May 28 - May 29
LEGOLAND Hotel NEW York
Business center

Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
2.0 star property
Central Valley
7.2 out of 10, Good, (1,004 reviews)
  • cleanliness
    Kids enjoy daytime adventures while parents relax in cozy rooms at this budget-friendly motel near Woodbury outlets.
The price is P5,239
P6,451 total
includes taxes & fees
Jun 2 - Jun 3
Americas Best Value Inn at Central Valley-Woodbury
Lobby

Best Western The Inn at Ramsey-Mahwah

Best Western The Inn at Ramsey-Mahwah
3.0 star property
Ramsey
7.2 out of 10, Good, (1,003 reviews)
  • cleanliness
    Family-friendly comfort with a wealth of complimentary amenities makes this hotel perfect for memorable trips with the little ones.
The price is P6,033
P6,915 total
includes taxes & fees
May 24 - May 25
Best Western The Inn at Ramsey-Mahwah
Reception

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Magical family escapes with a splash—seasonal outdoor pool near LEGOLAND® New York provides endless fun and relaxation.
The price is P8,579
P10,563 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites by Marriott Goshen Middletown
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.
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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"laundry on the first floor. The kitchen is equipped nicely."
KEN 2-night trip
Posted 8 hours ago
Sonesta Simply Suites Nanuet

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 LEGOLAND® New York, Galleria at Crystal Run, and Mount Peter Ski Area. Make sure you have lots of time for activities like Woodbury Common Premium Outlets and Orange County Fair Speedway.

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