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Check availability on Chester Family-Friendly Hotels

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

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, (48 reviews)
The price is ฿3,492
฿4,299 total
includes taxes & fees
21 Jun - 22 Jun
Comfort Suites Central Valley - Woodbury
Lobby

Quality Inn near Mountain Creek

Quality Inn near Mountain Creek
2.5 star property
Vernon
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Engaging hotel with mountain adventures for kids offers free breakfast and nearby waterpark thrills for all ages.
The price is ฿2,762
฿3,166 total
includes taxes & fees
28 May - 29 May
Quality Inn near Mountain Creek
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (164 reviews)
The price is ฿3,347
฿3,900 total
includes taxes & fees
25 May - 26 May
Borland House Inn
Free daily continental breakfast

Spark by Hilton Fishkill

Spark by Hilton Fishkill
3.0 star property
Fishkill
8.2 out of 10, Very good, (104 reviews)
The price is ฿3,027
฿3,500 total
includes taxes & fees
16 Jun - 17 Jun
Spark by Hilton Fishkill
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 ฿4,541
฿5,591 total
includes taxes & fees
26 May - 27 May
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,002 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 ฿3,305
฿3,904 total
includes taxes & fees
8 Jun - 9 Jun
Hampton Inn 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, (1,002 reviews)
The price is ฿3,999
฿4,724 total
includes taxes & fees
31 May - 1 Jun
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 ฿3,582
฿4,232 total
includes taxes & fees
31 May - 1 Jun
Courtyard by Marriott Middletown Goshen
Business centre

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, (1,000 reviews)
  • cleanliness
    Kids enjoy daytime adventures while parents relax in cosy rooms at this budget-friendly motel near Woodbury outlets.
The price is ฿3,267
฿4,022 total
includes taxes & fees
1 Jun - 2 Jun
Americas Best Value Inn at Central Valley-Woodbury
Free daily self-service 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, (1,001 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 ฿4,672
฿5,344 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
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

Holiday Inn Express Ramsey-Mahwah by IHG

Holiday Inn Express Ramsey-Mahwah by IHG

10/10 Excellent
"Staff were very friendly. Breakfast was decent. Rooms were very clean. Overall better than I expected."
Maryam 1-night trip
Posted less than an hour ago
Holiday Inn Express Ramsey-Mahwah by IHG

Frequently asked questions

What's Chester like for family-friendly holidays?
The welcoming destination of Chester is a great choice if you've been considering a holiday with the children. The excursions, swimming spots and coffee shops are just some of the things that make this an attractive spot for a family holiday. Take to the air and fly into Newburgh, NY (SWF-Stewart Intl.), which is located 13.5 mi (21.7 km) from the city centre.
What's the best family accommodation 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 holiday in Chester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What's there to see and do with your family in Chester?
While you are visiting Chester, you and the family may want to explore some interesting spots such as LEGOLAND® New York, Galleria at Crystal Run and Mount Peter Ski Area. Make sure that you have lots of time for activities such as Woodbury Common Premium Outlets and Orange County Fair Speedway.