A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Kid Friendly Hotels in Chester

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Check availability on Chester Family friendly Hotels

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chester family-friendly hotels

A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A boat ride with passengers holding binoculars, surrounded by water and themed structures.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
  • Family fun awaits with indoor pool, premium TV, and free breakfast at this hotel near Castle Fun Centre.
RM400
RM493 total
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express Hotel & Suites Chester by IHG
A large, two-story white house with a wrap-around porch and a small front garden.
A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.
A traditional living room with a chandelier, vintage furniture, and a fireplace.
A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
RM878
RM994 total
includes taxes & fees
12 Oct - 13 Oct
The Dominion House Bed & Breakfast
A hotel entrance with stone pillars, a covered walkway, and a bench.
A modern hotel room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.
A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.
A modern hotel lobby with seating areas, a bar, and a television screen.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe
RM448
RM507 total
includes taxes & fees
27 Oct - 28 Oct
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.
A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.

4. 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.
RM527
RM649 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A lobby with a fireplace, seating area, and a reception desk.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.
A hotel entrance with a covered area, a sign reading "Hampton Inn," and a clear sky.
A hotel room with a large bed, a sofa, a desk, and a bathroom.

5. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
RM483
RM594 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Harriman Woodbury
A swimming pool with colorful umbrellas and lounge chairs.
A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
A colorful play area with a check-in counter and a mascot.

6. 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.
RM442
RM1,057 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Hotel NEW York
A modern indoor space with two foosball tables, comfortable seating, and a TV screen.
An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.
A modern lounge area with seating, tables, and hanging chairs.
A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
RM332
RM392 total
includes taxes & fees
1 Nov - 2 Nov
Tru by Hilton Middletown
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A gym with treadmills, a weight bench, and various exercise equipment.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A modern bathroom with a large mirror, a sink, and a shower.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
RM462
RM546 total
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
RM466
RM550 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
A landscaped outdoor area with a fire feature, seating, and a pathway.
A modern bar area with a curved counter, bar stools, and a television screen.
A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

10. 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.
RM413
RM488 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Middletown Goshen
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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"😊"
Dorine 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Nanuet
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"This is my fourth visit to this location, and I plan to continue staying here in the future. The scenery is beautiful, the rooms are clean, the staff is wonderful, and everything is perfect."
debra a 2-night trip
Posted 1 day ago
Inn on the Hudson
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Very accommodating staff, they were able to move me to a room that didn't require stairs because I had a rolling cart with gear I needed to bring inside each night. I had to add a night to my reservation, so I bought another night there on Hotels.com, and they simply kept me in my same room so I didn't need to move anything. It was great! Good coffee available in the morning, easy location to get in and out of. They were actively renovating the property while I was there, so I don't count that towards the cleanliness of the property; everything was very clean, even while under renovation. Will stay again when needed!"
Brian 1-night trip
Posted 2 days ago
Ramada by Wyndham Newburgh/West Point
Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

10/10 Excellent
"Wonderful staff"
Julio 3-night trip
Posted 4 days ago
Studio 6 Extended Stay Fishkill Westage Center NY

Frequently asked questions

What's Chester like for family-friendly holidays?
The welcoming destination of Chester is a great choice if you've been considering a holiday with the children. The excursions, swimming spots and coffee shops are just some of the things that make this an attractive spot for a family holiday. Take to the air and fly into Newburgh, NY (SWF-Stewart Intl.), which is located 13.5 mi (21.7 km) from the city centre.
What's the best family accommodation 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 holiday in Chester?
The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What's there to see and do with your family in Chester?
While you are visiting Chester, you and the family may want to explore some interesting spots such as Sugar Loaf Performing Arts Center, Woodbury Common Premium Outlets and LEGOLAND® New York. Make sure that you have lots of time for activities such as Monroe Federal Plaza Shopping Center and Galleria at Crystal Run.

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