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Family friendly Hotels in Chester, New York

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Check availability on Chester Family friendly Hotels

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chester family-friendly hotels

A large, two-story white house with a wrap-around porch and a small front garden.
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.
A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.
A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
P13,432
P15,195 total
includes taxes & fees
Oct 1 - Oct 2
The Dominion House Bed & Breakfast
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.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.
A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.

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.
P7,435
P9,154 total
includes taxes & fees
Oct 26 - Oct 27
Fairfield Inn & Suites by Marriott Goshen Middletown
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A gym with exercise equipment, treadmills, and weight machines.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

3. 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.
P6,404
P7,564 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn by Hilton Middletown
A landscaped outdoor area with a fire feature, seating, and a pathway.
A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.
A modern bar area with a curved counter, bar stools, and a television screen.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

4. 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.
P6,585
P7,778 total
includes taxes & fees
Oct 12 - Oct 13
Courtyard by Marriott Middletown Goshen
A swimming pool with colorful umbrellas and lounge chairs.
A colorful play area with a check-in counter and a mascot.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.

5. 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.
P12,604
P23,070 total
includes taxes & fees
Oct 4 - Oct 5
LEGOLAND Hotel NEW York
Lobby
A spacious living area with a blue sofa, yellow armchair, and a coffee table. There is a TV mounted on a wooden shelf, and a kitchen area is visible in the background.
A modern hotel room with a kitchenette, a bed with white bedding, a seating area with a yellow ottoman, and a large window with curtains.
A hotel with a brick facade, a covered entrance, and a sign indicating it is a Comfort Suites hotel.

6. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
P7,206
P8,872 total
includes taxes & fees
Oct 29 - Oct 30
Comfort Suites Central Valley - Woodbury
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A hotel room with two beds, a desk, a TV, and a chair.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
P8,378
P9,897 total
includes taxes & fees
Sep 29 - Sep 30
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A bathroom with a white toilet, a bathtub, a shower, a sink with a mirror, and a towel rack.
A hotel room with a bed, a nightstand, a lamp, a painting on the wall, and two doors.
A reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.
A Super 8 motel sign with a parking lot and a building in the background.

8. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
P4,886
P5,771 total
includes taxes & fees
Sep 29 - Sep 30
Super 8 by Wyndham Middletown
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.
A hotel room with a wooden desk, a black TV, a lamp, and a chair.
A modern bathroom with a white bathtub, a vanity with a sink, and a large mirror.
A lobby with a reception desk, a sofa, a coffee table, and a dining area with chairs and a table.

9. 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.
P6,183
P7,614 total
includes taxes & fees
Oct 12 - Oct 13
Americas Best Value Inn at Central Valley-Woodbury
View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Was a pleasant overnight stay"
david 1-night trip
Posted 18 hours ago
Ramada by Wyndham Newburgh/West Point
Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

8/10 Good
"Everything was fine in the room, but the beds were too cranky and a little uncomfortable."
Young mi 2-night trip
Posted 22 hours ago
Hilton Garden Inn Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Beautiful and relaxing. Something I’d do different next time, I’d definitely stay at the Inn. As a solo female traveler, the Overlook was too secluded - it broke some of the solo traveling rules I’ve set for myself. Also, was a little bummed the next morning. Upon check in I was told about their Fall Foliage Buffet. I opted to do this instead of brunch the next day. Turns out that morning was a Princess Brunch, which canceled out the buffet and I had shown up after brunch hours. But the cafe was open and I was able to get a little something there."
Lindsay 1-night trip
Posted 1 day ago
Overlook Lodge at Bear Mountain
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Clean room, nice staff. Nice breakfast area added since I was last there. Very close to Paramount Theater and train station. Room had great view of the Hudson. Overall, a good overnight stay."
Laura 1-night trip
Posted 1 day ago
Inn on the Hudson
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

8/10 Good
"Nice hotel, needs a little updating."
Geraldine 2-night trip
Posted 2 days 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 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.

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