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

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Check availability on Chester Family Friendly Hotels

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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 garden with a stone fountain, a wooden gazebo, and various shrubs and 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
€209
includes taxes & fees
10 Sept - 11 Sept
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 Fairfield Inn & Suites hotel with a stone facade, a covered entrance, and a parking lot.
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.

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.
€142
includes taxes & fees
13 Sept - 14 Sept
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 Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.

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.
€99
includes taxes & fees
22 Sept - 23 Sept
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.
€103
includes taxes & fees
7 Sept - 8 Sept
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 restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.
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.
€319
includes taxes & fees
7 Sept - 8 Sept
LEGOLAND Hotel NEW York
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
€116
includes taxes & fees
31 Aug - 1 Sept
Comfort Suites Central Valley - Woodbury
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance 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 gym with treadmills, a weight bench, and various exercise equipment.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
€132
includes taxes & fees
30 Aug - 31 Aug
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 a wooden desk, a black TV, a lamp, and a chair.
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 cosy rooms at this budget-friendly motel near Woodbury outlets.
€105
includes taxes & fees
30 Aug - 31 Aug
Americas Best Value Inn at Central Valley-Woodbury
A bathroom with a white toilet, a bathtub, a shower, a sink with a mirror, and a towel rack.
A reception area with a counter, a clock, a no cash refunds sign, and a fire alarm.
A hotel room with a bed, a nightstand, a lamp, a painting on the wall, and two doors.
A lobby with a red sofa, two lamps, a coffee table with flowers, and a wall art piece.

9. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
€74
includes taxes & fees
20 Sept - 21 Sept
Super 8 by Wyndham Middletown
A two-story house with a porch, a front door, and a small garden area with potted plants.
A hallway with a wooden floor, a dining table with chairs, a lamp, and a framed picture on a side table.
A grand hallway with a wooden staircase, a patterned carpet, and a dining area with chairs and a table.
A sign for The Borland House, a bed and breakfast offering breakfast and brunch.

10. Borland House Inn

Borland House Inn
Montgomery
€109
includes taxes & fees
30 Aug - 31 Aug
Borland House Inn
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Choose what matters most at family-friendly hotels in Chester

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Chester Hotel Reviews

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

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

10/10 Excellent
"shshsn"
jay n 1-night trip
Posted 8 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

8/10 Good
"Really pleasant stay. Thank you"
graham 3-night trip
Posted 12 hours ago
Fairfield Inn & Suites by Marriott Goshen Middletown
Spark by Hilton Fishkill

Spark by Hilton Fishkill

10/10 Excellent
"Good"
Arthur 1-night trip
Posted 13 hours ago
Spark by Hilton Fishkill
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Room was clean and quiet. Breakfast was good and there was plenty of parking."
peter 3-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

10/10 Excellent
"Excellent stay from start to finish. It’s near nearby restaurants Chili’s, outback steakhouse and there’s an old-fashioned diner that was superb. This was one of the best things IExcellent stay from start to finish. It’s near nearby restaurants Chili’s, outback steakhouse and there’s a old-fashioned diner that was superb. This was one of the best days I had in the courtyard Marriott"
Tamara 3-night trip
Posted 15 hours ago
Courtyard by Marriott Middletown Goshen
Inn on the Hudson

Inn on the Hudson

8/10 Good
"I enjoyed it very much."
Michael 1-night trip
Posted 3 days ago
Inn on the Hudson
Studio 6 Extended Stay Fishkill Westage Center NY

Studio 6 Extended Stay Fishkill Westage Center NY

8/10 Good
"It was ok for the price."
Gregory 2-night trip
Posted 7 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 Gateway Plaza Shopping Center.