Find Family Hotels in Chester, NY

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Check availability on Chester Family Hotels

Tonight
18 Apr - 19 Apr
Tomorrow
19 Apr - 20 Apr
Next weekend
24 Apr - 26 Apr
In two weeks
1 May - 3 May

Our top choices for Chester family-friendly hotels

Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (34 reviews)
The price is AED 360
AED 444 total
includes taxes & fees
10 May - 11 May
Comfort Suites Central Valley - Woodbury
Suite, 1 King Bed, Non Smoking | Desk, iron/ironing board, free cribs/infant beds, rollaway beds

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, (1,003 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 AED 312
AED 361 total
includes taxes & fees
18 May - 19 May
Quality Inn & Suites Fishkill South near I-84
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,000 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 AED 340
AED 402 total
includes taxes & fees
29 Apr - 30 Apr
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 AED 339
AED 401 total
includes taxes & fees
30 Apr - 1 May
Hampton Inn by Hilton Middletown
Reception

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Magical family escapes with a splash—seasonal outdoor pool near LEGOLAND® New York provides endless fun and relaxation.
The price is AED 403
AED 496 total
includes taxes & fees
26 Apr - 27 Apr
Fairfield Inn & Suites by Marriott Goshen Middletown
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (158 reviews)
The price is AED 376
AED 438 total
includes taxes & fees
19 Apr - 20 Apr
Borland House Inn
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.0 out of 10, Very Good, (66 reviews)
The price is AED 359
AED 415 total
includes taxes & fees
7 May - 8 May
Spark by Hilton Fishkill
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (134 reviews)
The price is AED 691
AED 984 total
includes taxes & fees
19 Apr - 20 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Children's area

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Goshen
9.8 out of 10, Exceptional, (13 reviews)
The price is AED 545
AED 1,075 total
includes taxes & fees
20 Apr - 21 Apr
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Indoor pool

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,001 reviews)
  • cleanliness
    Indoor pool paradise with free cribs and laundry facilities at this family-focused hotel just minutes from Algonquin Park.
The price is AED 344
AED 389 total
includes taxes & fees
10 May - 11 May
Red Roof Inn & Suites Newburgh – Stewart Airport/ 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.
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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"Good place "
Tyrone 1-night trip
Posted 4 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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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.
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.