A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Chester Hotel Guide - Family Friendly Hotels in Chester, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Family Friendly Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chester family-friendly hotels

A hotel with a central entrance pavilion, a flag, and a landscaped garden.
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.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.

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.
€123
includes taxes & fees
10 Nov - 11 Nov
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 traditional living room with a chandelier, vintage furniture, and a fireplace.
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.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
€109
includes taxes & fees
9 Nov - 10 Nov
The Dominion House Bed & Breakfast
A hotel entrance with stone pillars, a covered walkway, and a bench.
A modern hotel lobby with seating areas, a bar, and a television screen.
A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.
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
€114
includes taxes & fees
1 Nov - 2 Nov
Sleep Inn & Suites Monroe - Woodbury
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 family inside an elevator with a blue patterned floor and a wall with cartoon characters.

4. 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.
€251
includes taxes & fees
18 Oct - 19 Oct
LEGOLAND Hotel NEW York
A modern indoor space with two foosball tables, comfortable seating, and a TV screen.
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.
A modern hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.

5. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
€86
includes taxes & fees
1 Nov - 2 Nov
Tru by Hilton Middletown
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A gym with exercise equipment, treadmills, and weight machines.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

6. 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.
€89
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn by Hilton Middletown
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.

7. 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.
€142
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
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 Courtyard by Marriott hotel with a sign, parking, and landscaped flower beds.
A modern hotel lobby with a seating area, large windows, and a television screen.

8. 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.
€107
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Middletown Goshen
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
€121
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
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 modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A gym with treadmills, a weight bench, and various exercise equipment.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
€115
includes taxes & fees
10 Nov - 11 Nov
La Quinta Inn & Suites by Wyndham 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

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"We have spent only 1 night but I will definitely come back to this hotel, we recommend it 👌"
Arie 1-night trip
Posted less than an hour ago
Hampton Inn & Suites Mahwah
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Very nicely organized. Loved the food too. Overall decorations were amazing. Definitely will recommend this hotel"
Meherun 1-night trip
Posted 1 hour ago
Crowne Plaza Suffern - Mahwah by IHG
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

8/10 Good
"Parking was great"
Kathie Campbell 3-night trip
Posted 17 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Friendly staff clean property nice amenities"
Rashean 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chester by IHG
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Common balcony was nice but it was a surprise."
joyce 1-night trip
Posted 2 days ago
Inn on the Hudson
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 9 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.