Black dirt region farm Chester New York

Find Family Hotels in Chester, NY

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Family Hotels

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, (55 reviews)
The price is ₩168,563
₩207,571 total
includes taxes & fees
Jun 21 - Jun 22
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, (1,014 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 ₩166,834
₩192,900 total
includes taxes & fees
Jul 13 - Jul 14
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, (1,005 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 ₩179,260
₩211,751 total
includes taxes & fees
Jun 28 - Jun 29
Courtyard by Marriott Middletown Goshen
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very Good, (127 reviews)
The price is ₩155,454
₩179,743 total
includes taxes & fees
Jul 13 - Jul 14
Spark by Hilton Fishkill
Exterior

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,018 reviews)
The price is ₩200,728
₩237,126 total
includes taxes & fees
Jun 16 - Jun 17
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,015 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 ₩180,549
₩213,273 total
includes taxes & fees
Jun 17 - Jun 18
Hampton Inn by Hilton Middletown
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (169 reviews)
The price is ₩243,392
₩283,599 total
includes taxes & fees
Jun 15 - Jun 16
Borland House Inn
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, (1,001 reviews)
  • cleanliness
    Magical family escapes with a splash—seasonal outdoor pool near LEGOLAND® New York provides endless fun and relaxation.
The price is ₩218,480
₩269,003 total
includes taxes & fees
Jun 16 - Jun 17
Fairfield Inn & Suites by Marriott Goshen 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, (51 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 ₩661,921
₩966,257 total
includes taxes & fees
Jul 8 - Jul 9
LEGOLAND Hotel NEW York
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, (1,014 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 ₩167,638
₩192,155 total
includes taxes & fees
Jun 21 - Jun 22
Best Western The Inn at Ramsey-Mahwah
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

Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

6/10 Okay
"The rooms and the hallways needs to be updated .. The whole building needs to be upgraded. The staff at the front desk was helpful and nice. That’s the only thing that this place had going for it I won’t be staying here next visit"
Lynne 1-night trip
Posted 4 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, Woodbury Common Premium Outlets, 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.