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Find Family Hotels in Chester, NY

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Check availability on Chester Family Hotels

Tonight
Sep 8 - Sep 9
Tomorrow
Sep 9 - Sep 10
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chester family-friendly hotels

Exterior
Miscellaneous
Superior Double Room, Ensuite (Primrose) | Miscellaneous
Miscellaneous

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
NT$6,783
NT$7,673 total
includes taxes & fees
Sep 14 - Sep 15
The Dominion House Bed & Breakfast
Reception
Terrace/patio
Restaurant
Lobby

2. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen
  • Magical family escapes with a splash—seasonal outdoor pool near LEGOLAND® New York provides endless fun and relaxation.
NT$4,070
NT$5,011 total
includes taxes & fees
Oct 7 - Oct 8
Fairfield Inn & Suites by Marriott Goshen Middletown
Property amenity
Lobby
Property amenity
Lobby

3. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
  • Splash into family-friendly fun at this stylish hotel with an indoor pool, on-site bistro, and prime location near LEGOLAND® New York.
NT$3,191
NT$3,770 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott Middletown Goshen
Lobby
Fitness facility
Exterior
Room

4. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
  • Family fun at Hampton Inn by Hilton Middletown starts with a seasonal pool and LEGOLAND® just a short drive away.
NT$3,106
NT$3,669 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn by Hilton Middletown
Exterior
Bathroom
Fitness facility
Room

5. La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
NT$4,231
NT$4,998 total
includes taxes & fees
Sep 13 - Sep 14
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Lobby
Suite, Multiple Beds, Non Smoking
Lobby
Breakfast area

6. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
NT$3,673
NT$4,522 total
includes taxes & fees
Sep 21 - Sep 22
Comfort Suites Central Valley - Woodbury
Business center
Room, 2 Double Beds, Non Smoking
Bathroom
Room

7. Americas Best Value Inn at Central Valley-Woodbury

Americas Best Value Inn at Central Valley-Woodbury
Central Valley
  • Kids enjoy daytime adventures while parents relax in cozy rooms at this budget-friendly motel near Woodbury outlets.
NT$3,123
NT$3,846 total
includes taxes & fees
Sep 9 - Sep 10
Americas Best Value Inn at Central Valley-Woodbury
Pool
Lobby
Ninjago Premium Themed
Breakfast area

8. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
  • Splash into family adventure at LEGOLAND Hotel with an outdoor pool, playground, and game room full of toys for endless fun.
NT$9,341
NT$15,178 total
includes taxes & fees
Oct 4 - Oct 5
LEGOLAND Hotel NEW York
Exterior detail
Interior detail
Lobby
Exterior detail

9. Borland House Inn

Borland House Inn
Montgomery
NT$3,233
NT$3,933 total
includes taxes & fees
Sep 13 - Sep 14
Borland House Inn
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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

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 Gateway Plaza Shopping Center.

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