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

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Check availability on Chester Family-Friendly Hotels

Tonight
8 Oct - 9 Oct
Tomorrow
9 Oct - 10 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 hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A Simon Premium Outlet sign at Woodbury Commons.
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.
฿3,398
฿4,184 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 dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.
A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
฿7,228
฿8,176 total
includes taxes & fees
14 Oct - 15 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 modern hotel lobby with seating areas, a bar, and a television screen.
A hotel room with a bed, a sofa, a desk, and a large window with curtains.

3. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe
฿3,686
฿4,170 total
includes taxes & fees
28 Oct - 29 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.
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.

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.
฿4,337
฿5,339 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A lobby with a fireplace, seating area, and a reception desk.
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.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.

5. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
฿3,975
฿4,894 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 colorful play area with a check-in counter and a mascot.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.

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.
฿3,639
฿8,701 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.
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.
A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
฿2,729
฿3,224 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 bathroom with a large mirror, a sink, and a shower.
A hotel room with two beds, a desk, a TV, and a chair.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
฿3,800
฿4,489 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.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.
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
฿3,836
฿4,531 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A conference room with multiple tables and chairs, a projector screen, and a green accent wall.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A modern restaurant with a central island, multiple tables, and chairs.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
฿5,405
฿6,503 total
includes taxes & fees
26 Oct - 27 Oct
Home2 Suites by Hilton Middletown
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

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

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

8/10 Good
"My stay was nice I did here a couple arguing a few rooms down"
Kakia 1-night trip
Posted 12 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"A+"
Kanwarpreet 2-night trip
Posted 15 hours ago
Overlook Lodge at Bear Mountain
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 3 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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