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Check availability on Chester Family-Friendly Hotels

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
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 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.

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 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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

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.
฿4,378
฿5,390 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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

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 hotel lobby with a seating area, large windows, and a television screen.
A modern bar area with a curved counter, bar stools, and a television screen.

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 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.

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 hotel room with two beds, a desk, a TV, and a chair.
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.

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 hotel room with a wooden desk, a black TV, a lamp, and a chair.
A hotel room with two beds, a nightstand, a lamp, and artwork on the walls.
A modern bathroom with a white bathtub, a vanity with a sink, and a large mirror.

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
24 Aug - 25 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 lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.
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.

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 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.
A hallway with a wooden floor, a dining table with chairs, a lamp, and a framed picture on a side table.
A grand hallway with a wooden staircase, a patterned carpet, and a dining area with chairs and a table.

10. Borland House Inn

Borland House Inn
Montgomery
฿3,347
฿3,900 total
includes taxes & fees
24 Aug - 25 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

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 less than an hour ago
Spark by Hilton Fishkill
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"The staff made my day. They all display true hospitality and made each day better. Thank you so much."
Tiffany 3-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Mountain Creek

Mountain Creek

10/10 Excellent
"Great place for a quick get away. It’s within walking distance of the Water Park and close to other resorts and restaurants. Loved the room that was provided to us and the heated pool. Will definitely come back to this resort."
Rosanna 2-night trip
Posted 2 hours ago
Mountain Creek
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 1 day 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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