Find Family Hotels in Chester, NY

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Check availability on Chester Family Hotels

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

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)
"Brand new hotel. Quiet. Helpful staff. Large room, comfortable bed. Woodbury Commons shopping less than 5 minute drive and close to NYC. Will stay here again."
Canada
Constantinos
The price is NT$3,355
NT$4,131 total
includes taxes & fees
Jun 4 - Jun 5
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.
"This is a family-owned property. We have been staying there every year for the special Olympic events. The hosts are friendly and very welcoming "
United States
Margaret
The price is NT$2,668
NT$3,058 total
includes taxes & fees
May 28 - May 29
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)
"What a wonderful experience staying at the Borland House is! With the quaint, homey feeling of the whole house, to the kindness of the staff. Your stay will absolutely be lovely. Ample towels are provided for the private, spacious bathroom. Very comfortable bedding and well appointed decorations are in the bedroom. I was in the Hummingbird Suite. I could see myself living there, it just had everything I needed. I look forward to visiting again in the future!"
United States
Elizabeth
The price is NT$3,233
NT$3,767 total
includes taxes & fees
May 25 - May 26
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)
"clean room, quiet, nearby to restaurants"
United States
Reginald
The price is NT$2,923
NT$3,380 total
includes taxes & fees
Jun 16 - Jun 17
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.
"Clean, safe for families"
Canada
Liliana
The price is NT$4,386
NT$5,400 total
includes taxes & fees
May 26 - May 27
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 amenities were spotless, beautiful, and super well organized! My son absolutely loved the breakfast options. Our stay was truly amazing and incredibly enjoyable!"
United States
Ana Maria
The price is NT$3,192
NT$3,770 total
includes taxes & fees
Jun 8 - Jun 9
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)
"Great area for family fun"
United States
harold
The price is NT$3,862
NT$4,562 total
includes taxes & fees
May 31 - Jun 1
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.
"I always enjoy my stay here when I come to visit family!"
United States
Yasmin
The price is NT$3,460
NT$4,087 total
includes taxes & fees
May 31 - Jun 1
Courtyard by Marriott Middletown Goshen
Business center

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, (1,001 reviews)
  • cleanliness
    Kids enjoy daytime adventures while parents relax in cozy rooms at this budget-friendly motel near Woodbury outlets.
"I feel like they are family now after having stayed there multiple times."
United States
Pamela
The price is NT$3,155
NT$3,885 total
includes taxes & fees
Jun 1 - Jun 2
Americas Best Value Inn at Central Valley-Woodbury
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, (1,001 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.
"Went there for one night with my family and the room was spacious, clean and quiet."
United States
Mayra
The price is NT$5,017
NT$5,738 total
includes taxes & fees
May 26 - May 27
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.
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

6/10 Okay
"The lack of snacks and soft drinks available for purchase unless you have change was very inconvenient; otherwise, hotel was adequate for our trip."
Kim 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel 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, 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.

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