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Check availability on Chester Family Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

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 swimming pool with a deck, surrounded by potted plants and outdoor furniture.

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
NT$6,783
NT$7,674 total
includes taxes & fees
Sep 28 - Sep 29
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.
NT$3,924
NT$4,831 total
includes taxes & fees
Sep 13 - Sep 14
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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
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.
NT$3,087
NT$3,646 total
includes taxes & fees
Sep 23 - Sep 24
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 hotel lobby with a fireplace, comfortable seating, and a television.
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.
NT$3,459
NT$4,086 total
includes taxes & fees
Sep 20 - Sep 21
Courtyard by Marriott Middletown Goshen
A swimming pool with colorful umbrellas and lounge chairs.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
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.

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.
NT$6,575
NT$11,899 total
includes taxes & fees
Oct 4 - Oct 5
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.
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.

6. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
NT$3,633
NT$4,473 total
includes taxes & fees
Sep 21 - Sep 22
Comfort Suites Central Valley - Woodbury
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 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
NT$4,231
NT$4,998 total
includes taxes & fees
Sep 14 - Sep 15
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 two beds, a nightstand, a lamp, and artwork on the walls.
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 cozy rooms at this budget-friendly motel near Woodbury outlets.
NT$3,123
NT$3,846 total
includes taxes & fees
Sep 13 - Sep 14
Americas Best Value Inn at Central Valley-Woodbury
A two-story house with a porch, a front door, and a small garden area with potted plants.
A grand hallway with a wooden staircase, a patterned carpet, and a dining area with chairs and a table.
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 sign for The Borland House, a bed and breakfast offering breakfast and brunch.

9. Borland House Inn

Borland House Inn
Montgomery
NT$3,242
NT$3,944 total
includes taxes & fees
Sep 13 - Sep 14
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

Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Very friendly and clean, very nice view of the river would recommend room with balcony on 2nd floor for the nice view"
Ryan 1-night trip
Posted 5 hours ago
Inn on the Hudson
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

10/10 Excellent
"A nice clean hotel with good staff. No complaints"
Diraige 5-night trip
Posted 11 hours ago
Fairfield Inn & Suites by Marriott Goshen Middletown
Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

10/10 Excellent
"It was a lot cleaner inside and outside since I was there in June the lady at the desk was great even though some crazy lady was screaming at her and lying to anyone who would listen to her and threating people that woman at the desk was the nicest and most professional person I have ever met I look forward to returning and staying there"
Tim 2-night trip
Posted 2 days ago
Studio 6 Extended Stay Fishkill Westage Center NY
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Beautiful place !"
Christian 2-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

10/10 Excellent
"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."
Adrienne 1-night trip
Posted 4 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

10/10 Excellent
"Very good."
Ibrahim 1-night trip
Posted 4 days ago
Courtyard by Marriott Mahwah

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 Gateway Plaza Shopping Center and Galleria at Crystal Run.

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