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Check availability on Chester Family Hotels

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Chester family-friendly hotels

A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A Simon Premium Outlet sign at Woodbury Commons.
A boat ride with passengers holding binoculars, surrounded by water and themed structures.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

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 Center.
NT$3,287
NT$4,048 total
includes taxes & fees
Oct 27 - Oct 28
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 swimming pool with a deck, surrounded by potted plants and outdoor furniture.
A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.
A traditional living room with a chandelier, vintage furniture, and a fireplace.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
NT$3,499
NT$3,958 total
includes taxes & fees
Nov 9 - Nov 10
The Dominion House Bed & Breakfast
A hotel entrance with stone pillars, a covered walkway, and a bench.
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.
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
NT$3,464
NT$3,919 total
includes taxes & fees
Nov 15 - Nov 16
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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.
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.
NT$4,199
NT$5,170 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.
A LEGO display with a large red sign reading 'BRICKS RECIPE BOOK' by S. Platt, featuring LEGO figures and a colorful LEGO building.
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.
NT$4,145
NT$9,159 total
includes taxes & fees
Oct 25 - Oct 26
LEGOLAND Hotel NEW York
A lobby with a fireplace, seating area, and a reception desk.
An outdoor patio with brick flooring, round tables, and blue umbrellas.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.
A hotel room with a large bed, a sofa, a desk, and a bathroom.

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
NT$3,846
NT$4,735 total
includes taxes & fees
Nov 9 - Nov 10
Hampton Inn Harriman Woodbury
A hotel with a modern facade, multiple floors, and a covered entrance area.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
A lobby area with a reception desk, seating arrangements, and large windows.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
NT$3,847
NT$4,544 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express & Suites Middletown - Goshen by IHG
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 reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.
A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

8. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
NT$2,482
NT$2,932 total
includes taxes & fees
Nov 8 - Nov 9
Tru by Hilton Middletown
A hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.
A hotel lobby with orange seating, a dining area, and a TV screen.
A pool area with a hot tub, a pool lift, and safety signs on the walls.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
NT$3,464
NT$4,092 total
includes taxes & fees
Nov 18 - Nov 19
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 modern hotel lobby with a seating area, large windows, and a television screen.
A Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.

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.
NT$3,298
NT$3,895 total
includes taxes & fees
Nov 8 - Nov 9
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

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

8/10 Good
"Overall a great hotel to stay at and a great value. Location is ideal for anything you need to do. They definitely need to improve the quality and variety of their breakfast."
Charles 4-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Bathroom needed updating, tub peeling, ceiling peeling. Bed comfortable, location perfect, parking easy. Ice machine was not where welcome book indicated."
Deborah 1-night trip
Posted 6 hours ago
Inn on the Hudson
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

8/10 Good
"They have begun to charge $10 to park on the property which is kind of ridiculous , not to many happy guests with the new policy."
greg 1-night trip
Posted 3 days ago
Crowne Plaza Suffern - Mahwah by IHG
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Was under construction, room was clean and comfortable."
Gary 4-night trip
Posted 4 days ago
Ramada by Wyndham Newburgh/West Point

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 Monroe Federal Plaza Shopping Center and Galleria at Crystal Run.

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