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Check availability on Chester Family-Friendly Hotels

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

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 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.
₹9,577
₹11,792 total
includes taxes & fees
27 Oct - 28 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 traditional living room with a chandelier, vintage furniture, and a fireplace.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
₹10,194
₹11,532 total
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 room with a flat-screen TV, a fireplace, a desk with a computer, and comfortable seating.
A covered outdoor area with a fire pit, wooden chairs, and a view of a building with multiple windows.
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
₹10,075
₹11,398 total
includes taxes & fees
15 Nov - 16 Nov
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 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.

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.
₹12,186
₹15,005 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.
A colorful play area with a check-in counter and a mascot.
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.

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.
₹12,030
₹26,582 total
includes taxes & fees
1 Nov - 2 Nov
LEGOLAND Hotel NEW York
A lobby with a fireplace, seating area, and a reception desk.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.
An outdoor patio with brick flooring, round tables, and blue umbrellas.
A hotel entrance with a covered area, a sign reading "Hampton Inn," and a clear sky.

6. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
₹11,204
₹13,795 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Harriman Woodbury
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 hotel with a prominent 'tru by Hilton' sign, a covered entrance, and a well-lit facade.
An outdoor seating area with a blue sofa, round table, and chairs, under a canopy with string lights.

7. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
₹7,231
₹8,542 total
includes taxes & fees
8 Nov - 9 Nov
Tru by Hilton Middletown
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.
A lobby area with a reception desk, seating arrangements, and large windows.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
₹11,147
₹13,168 total
includes taxes & fees
26 Oct - 27 Oct
Holiday Inn Express & Suites Middletown - Goshen by IHG
A modern hotel with a prominent 'LA QUINTA' sign, a covered entrance, and a parking area.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A modern bathroom with a large mirror, a sink, and a shower.
A pool area with a hot tub, a pool lift, and safety signs on the walls.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
₹10,156
₹11,997 total
includes taxes & fees
10 Nov - 11 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 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.
₹9,556
₹11,287 total
includes taxes & fees
8 Nov - 9 Nov
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

10/10 Excellent
"Nice, laid back hotel with great staff."
William 4-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Slightly dated hotel walkable into the town centre have used before and would use again"
Paul 1-night trip
Posted 2 days 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 2 days ago
Crowne Plaza Suffern - Mahwah by IHG
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

8/10 Good
"I thought it was very helpful that they had breakfast bags to go for those of us that couldn't get to the breakfast."
Vicky Lynn 1-night trip
Posted 3 days ago
Hampton Inn & Suites Mahwah
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 3 days ago
Ramada by Wyndham Newburgh/West Point

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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