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Check availability on Chester Family-Friendly Hotels

Tonight
24 Aug - 25 Aug
Tomorrow
25 Aug - 26 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

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 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.
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
฿7,024
฿7,946 total
includes taxes & fees
7 Sept - 8 Sept
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.
฿4,214
฿5,189 total
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites by Marriott Goshen Middletown
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A gym with exercise equipment, treadmills, and weight machines.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

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.
฿3,188
฿3,766 total
includes taxes & fees
31 Aug - 1 Sept
Hampton Inn by Hilton Middletown
A landscaped outdoor area with a fire feature, seating, and a pathway.
A modern hotel lobby with a fireplace, comfortable seating, and a television.
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.

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.
฿3,305
฿3,904 total
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Middletown Goshen
A swimming pool with colorful umbrellas and lounge chairs.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.
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.

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.
฿6,591
฿12,064 total
includes taxes & fees
7 Sept - 8 Sept
LEGOLAND Hotel NEW York
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
฿3,600
฿4,433 total
includes taxes & fees
30 Aug - 31 Aug
Comfort Suites Central Valley - Woodbury
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A modern bathroom with a large mirror, a sink, and a shower.
A gym with treadmills, a weight bench, and various exercise equipment.
A hotel room with two beds, a desk, a TV, and a chair.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
฿4,058
฿4,793 total
includes taxes & fees
30 Aug - 31 Aug
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A hotel lobby with two sofas, a coffee machine, and a view of the parking lot.
A modern bathroom with a white bathtub, a vanity with a sink, and a large mirror.
A hotel room with a wooden desk, a black TV, a lamp, and a chair.
A lobby with a reception desk, a sofa, a coffee table, and a dining area with chairs and a table.

8. 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 cosy rooms at this budget-friendly motel near Woodbury outlets.
฿3,234
฿3,982 total
includes taxes & fees
25 Aug - 26 Aug
Americas Best Value Inn at Central Valley-Woodbury
A bathroom with a white toilet, a bathtub, a shower, a sink with a mirror, and a towel rack.
A Super 8 motel sign with a parking lot and a building in the background.
A reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.
A hotel room with a bed, a nightstand, a lamp, a painting on the wall, and two doors.

9. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
฿2,389
฿2,821 total
includes taxes & fees
30 Aug - 31 Aug
Super 8 by Wyndham Middletown
A two-story house with a porch, a front door, and a small garden area with potted plants.
A hallway with a wooden floor, a dining table with chairs, a lamp, and a framed picture on a side table.
A sign for The Borland House, a bed and breakfast offering breakfast and brunch.
A cozy living room with a sofa, armchair, and a table with a vase. A chandelier hangs from the ceiling, and there are framed pictures on the walls.

10. Borland House Inn

Borland House Inn
Montgomery
฿3,550
฿4,137 total
includes taxes & fees
25 Aug - 26 Aug
Borland House Inn
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Great place to stay. It was my first time staying there and will stay again when in the area."
Keith 1-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Mountain Creek

Mountain Creek

10/10 Excellent
"Very convenient location to many fun activities for the entire family. Staff were helpful, rooms clean and comfortable. I would definitely recommend this place for fun all."
Mellisa 3-night trip
Posted 9 hours ago
Mountain Creek
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"I enjoyed my stay at the DoubleTree. From the time we entered the hotel, the staff were friendly, room was clean, it was up to date, enjoyed the pool and the yummy cookies."
Cloraine 2-night trip
Posted 10 hours ago
DoubleTree by Hilton Hotel Nanuet
Spark by Hilton Fishkill

Spark by Hilton Fishkill

10/10 Excellent
"The staff was courteous and helpful. Will definitely stay there again some time in the future."
Rahul 3-night trip
Posted 10 hours ago
Spark by Hilton Fishkill
Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

8/10 Good
"It was ok for the price."
Gregory 2-night trip
Posted 2 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 Gateway Plaza Shopping Center.

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