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

Find Family Hotels in Chester, NY from CA $135

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Check availability on Chester Family Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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.

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
CA $304
CA $344 total
includes taxes & fees
Oct 21 - Oct 22
The Dominion House Bed & Breakfast
A wooden deck with wicker chairs and a hot tub.
A backyard with a pool, outdoor seating, and a fire pit.
Exterior
A bedroom with a large bed, a sofa, a bedside table, and a window.

2. Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres

Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres
Chester
CA $2,473
CA $4,195 total
includes taxes & fees
Oct 1 - Oct 2
Spacious villa w/Pool, Hot Tub & Game Room on 7.5 private acres
A swimming pool with clear blue water, surrounded by trees and white fencing.
A spacious hallway with a wooden floor, a golden chair, and a staircase with white railings.
A hot tub with a wooden deck and railing, surrounded by a grassy area and a stone wall.
A large stone house with a dark roof, surrounded by lush green trees and a well-maintained lawn.

3. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
CA $2,444
CA $4,088 total
includes taxes & fees
Sep 30 - Oct 1
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
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.

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.
CA $168
CA $207 total
includes taxes & fees
Oct 27 - Oct 28
Fairfield Inn & Suites by Marriott Goshen Middletown
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A hotel room with two beds, a desk, a TV, and a chair.
A modern bathroom with a large mirror, a sink, and a shower.
A gym with treadmills, a weight bench, and various exercise equipment.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
CA $190
CA $224 total
includes taxes & fees
Oct 26 - Oct 27
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

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.
CA $143
CA $169 total
includes taxes & fees
Oct 28 - Oct 29
Hampton Inn by Hilton Middletown
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.

7. 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.
CA $143
CA $169 total
includes taxes & fees
Oct 28 - Oct 29
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 colorful play area with a check-in counter and a mascot.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.

8. 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.
CA $285
CA $522 total
includes taxes & fees
Oct 25 - Oct 26
LEGOLAND Hotel NEW York
Lobby
A hotel with a brick facade, a covered entrance, and a sign indicating it is a Comfort Suites hotel.
Breakfast area
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.

9. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
CA $167
CA $206 total
includes taxes & fees
Oct 5 - Oct 6
Comfort Suites Central Valley - Woodbury
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
A modern restaurant with a central island, multiple tables, and chairs.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
CA $169
CA $205 total
includes taxes & fees
Oct 26 - Oct 27
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

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

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

8/10 Good
"le prix"
Hugues 1-night trip
Posted less than an hour ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

10/10 Excellent
"Great stay"
Danny 1-night trip
Posted 2 hours ago
Hilton Garden Inn Nanuet
Sonesta Simply Suites Nanuet

Sonesta Simply Suites Nanuet

10/10 Excellent
"A great place for short and long stay. I have plenty of room to even study and work remotely. in house laundry, a great hard working staff makes this place a great choice. Is very quiet as ins unique location which allows me to rest even during the day. STORM PROOF as I had stayed at other places where the ceiling leaked etc, not SONESTA SIMPLY SUITS. Extremely well designed as I previously noted relating the water treatment work previously to from its design. A+++"
Eric 3-night trip
Posted 10 hours ago
Sonesta Simply Suites Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Very peaceful"
Michael 1-night trip
Posted 20 hours ago
Overlook Lodge at Bear Mountain
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Was a pleasant overnight stay"
david 1-night trip
Posted 2 days ago
Ramada by Wyndham Newburgh/West Point
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

8/10 Good
"Nice hotel, needs a little updating."
Geraldine 2-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Nanuet

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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