Family friendly Hotels in Chester, New York

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Check prices for these dates

Tonight
Nov 13 - Nov 14
Tomorrow
Nov 14 - Nov 15
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Chester family-friendly hotels

A Holiday Inn Express hotel with a covered entrance, stone facade, and a clear sky.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Family fun awaits with indoor pool, premium TV, and free breakfast at this hotel near Castle Fun Center.
The price is P6,895
P8,489 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Chester by IHG
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (241 reviews)
The price is P13,600
P15,385 total
includes taxes & fees
Nov 16 - Nov 17
The Dominion House Bed & Breakfast
A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,128 reviews)
The price is P7,262
P8,215 total
includes taxes & fees
Nov 24 - Nov 25
Sleep Inn & Suites Monroe - Woodbury
A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

4. 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 P8,160
P10,047 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Goshen Middletown
A colorful LEGO-themed building with a prominent LEGO logo.

5. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (139 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 P5,638
P14,944 total
includes taxes & fees
Nov 20 - Nov 21
LEGOLAND Hotel NEW York
A hotel entrance with a covered area, a sign reading "Hampton Inn," and a clear sky.

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,152 reviews)
  • cleanliness
    Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
The price is P6,990
P8,606 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn Harriman Woodbury
A modern hotel building with a prominent sign, a covered entrance, and a parking area.

7. 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, (1,001 reviews)
The price is P7,151
P8,447 total
includes taxes & fees
Dec 6 - Dec 7
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A modern indoor space with two foosball tables, comfortable seating, and a TV screen.

8. Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
The price is P5,228
P6,176 total
includes taxes & fees
Nov 29 - Nov 30
Tru by Hilton Middletown
A lobby area with seating, a reception desk, and a refrigerator stocked with beverages.

9. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (796 reviews)
The price is P6,072
P7,173 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Middletown - Goshen by IHG
An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (799 reviews)
The price is P9,624
P11,590 total
includes taxes & fees
Nov 19 - Nov 20
Home2 Suites by Hilton Middletown
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

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, Woodbury Common Premium Outlets, and LEGOLAND® New York. Make sure you have lots of time for activities like Monroe Federal Plaza Shopping Center and Galleria at Crystal Run.