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Find Family Hotels in Chester, NY

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Check availability on Chester Family Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chester family-friendly hotels

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

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, (1,001 reviews)
  • cleanliness
    Family fun awaits with indoor pool, premium TV, and free breakfast at this hotel near Castle Fun Center.
The price is ₩143,373
₩176,527 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express Hotel & Suites Chester by IHG
A large, two-story white house with a wrap-around porch and a small front garden.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (239 reviews)
The price is ₩142,713
₩161,445 total
includes taxes & fees
Nov 11 - Nov 12
The Dominion House Bed & Breakfast
A hotel entrance with stone pillars, a covered walkway, and a bench.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
2.5 star property
Monroe
9.4 out of 10, Exceptional, (1,113 reviews)
The price is ₩142,368
₩161,055 total
includes taxes & fees
Nov 22 - Nov 23
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, (1,000 reviews)
  • cleanliness
    Magical family escapes with a splash—seasonal outdoor pool near LEGOLAND® New York provides endless fun and relaxation.
The price is ₩171,255
₩210,857 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.

5. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (136 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 ₩170,627
₩377,036 total
includes taxes & fees
Nov 1 - Nov 2
LEGOLAND Hotel NEW York
A lobby with a fireplace, seating area, and a reception desk.

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 ₩156,851
₩193,124 total
includes taxes & fees
Nov 10 - Nov 11
Hampton Inn Harriman Woodbury
A modern indoor space with two foosball tables, comfortable seating, and a TV screen.

7. 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 ₩108,776
₩128,491 total
includes taxes & fees
Nov 29 - Nov 30
Tru by Hilton Middletown
A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.

8. 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, (1,000 reviews)
The price is ₩150,081
₩177,284 total
includes taxes & fees
Nov 22 - Nov 23
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A hotel with a modern facade, multiple floors, and a covered entrance area.

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, (789 reviews)
The price is ₩147,392
₩174,106 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn Express & Suites Middletown - Goshen by IHG
A landscaped outdoor area with a fire feature, seating, and a pathway.

10. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,003 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 ₩134,283
₩158,621 total
includes taxes & fees
Nov 9 - Nov 10
Courtyard by Marriott Middletown Goshen
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"It was a great location and the hotel is clean and well maintained."
bhargavi 1-night trip
Posted 1 day ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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.