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Check availability on Chester Family Hotels

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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 ₩312,771
₩353,824 total
includes taxes & fees
Aug 3 - Aug 4
The Dominion House Bed & Breakfast
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 ₩209,484
₩257,927 total
includes taxes & fees
Aug 2 - Aug 3
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very Good, (1,000 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 ₩155,073
₩183,180 total
includes taxes & fees
Aug 10 - Aug 11
Hampton Inn by Hilton Middletown
Courtyard

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (779 reviews)
The price is ₩293,103
₩351,319 total
includes taxes & fees
Aug 11 - Aug 12
Home2 Suites by Hilton Middletown
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, (1,011 reviews)
The price is ₩179,371
₩211,882 total
includes taxes & fees
Aug 16 - Aug 17
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Free daily self-serve breakfast

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
2.5 star property
Peekskill
9.2 out of 10, Wonderful, (1,013 reviews)
  • cleanliness
    Discover a family adventure haven where kids can splash and play all day, just steps from scenic park trails and Hudson River views.
The price is ₩181,931
₩208,083 total
includes taxes & fees
Aug 2 - Aug 3
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
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 ₩165,696
₩195,728 total
includes taxes & fees
Aug 26 - Aug 27
Courtyard by Marriott Middletown Goshen
View from property

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (338 reviews)
The price is ₩312,771
₩369,460 total
includes taxes & fees
Aug 6 - Aug 7
Residence Inn by Marriott Middletown Goshen
Suite, 1 King Bed, Non Smoking | Desk, iron/ironing board, cribs (free), rollaway beds (surcharge)

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, (1,000 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 ₩162,554
₩187,954 total
includes taxes & fees
Aug 9 - Aug 10
Quality Inn & Suites Fishkill South near I-84
Lobby

Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
2.5 star property
Central Valley
8.4 out of 10, Very Good, (92 reviews)
The price is ₩161,899
₩199,337 total
includes taxes & fees
Aug 12 - Aug 13
Comfort Suites Central Valley - Woodbury
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

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"good stay"
James 1-night trip
Posted 4 hours ago
Hampton Inn Harriman Woodbury

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 Woodbury Common Premium Outlets. Make sure you have lots of time for activities like Gateway Plaza Shopping Center and Galleria at Crystal Run.