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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 modern hotel lobby with a large map mural, seating areas, and a reception desk.
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 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.
A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
฿7,228
฿8,176 total
includes taxes & fees
20 Oct - 21 Oct
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 modern hotel room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.

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 spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

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 room with a large bed, a sofa, a desk, and a bathroom.
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.

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 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.

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 hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

7. 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 modern indoor space with two foosball tables, comfortable seating, and a TV screen.
An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.
A modern reception area with a curved wooden counter, seating area with colorful cushions, and pendant lighting.
A modern lounge area with seating, tables, and hanging chairs.

8. 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 modern bathroom with a large mirror, a sink, and a shower.
A hotel room with two beds, a desk, a TV, and a chair.
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
฿3,800
฿4,489 total
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Très belle hotel je recommende"
Danny 1-night trip
Posted less than an hour ago
Crowne Plaza Suffern - Mahwah by IHG
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Beautiful room nice and comfortable! Beautiful view out from the window"
James 3-night trip
Posted 6 hours ago
Inn on the Hudson
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 20 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 23 hours ago
Overlook Lodge at Bear Mountain
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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