Chester Hotel Guide - Family Friendly Hotels in Chester, New York

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Check availability on Chester Family Friendly Hotels

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 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
8.2 out of 10, Very good, (49 reviews)
The price is €108
includes taxes & fees
8 Jun - 9 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 €83
includes taxes & fees
2 Jun - 3 Jun
Quality Inn near Mountain Creek
Property amenity

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,001 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 €115
includes taxes & fees
14 Jun - 15 Jun
Courtyard by Marriott Middletown Goshen
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 €152
includes taxes & fees
1 Jun - 2 Jun
Fairfield Inn & Suites by Marriott Goshen 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 €134
includes taxes & fees
3 Jun - 4 Jun
La Quinta Inn & Suites by Wyndham 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, (115 reviews)
The price is €92
includes taxes & fees
21 Jun - 22 Jun
Spark by Hilton Fishkill
Lobby

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (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 €102
includes taxes & fees
8 Jun - 9 Jun
Hampton Inn by Hilton Middletown
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, (138 reviews)
The price is €289
includes taxes & fees
4 Jun - 5 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Borland House Inn

Borland House Inn
3.0 star property
Montgomery
9.2 out of 10, Wonderful, (166 reviews)
The price is €171
includes taxes & fees
1 Jun - 2 Jun
Borland House Inn
Reception

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Family-friendly hotel with indoor pool offers all-day fun just minutes from SplashDown Beach water park attractions.
The price is €125
includes taxes & fees
7 Jun - 8 Jun
Hilton Garden Inn Fishkill
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

Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

2/10 Terrible
"Hotel was overbooked so I had to find another room at short notice. Staff was very rude when I inquired about a refund."
Jeffrey 1-night trip
Posted 4 hours ago
Studio 6 Extended Stay Fishkill Westage Center NY

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.