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 $137

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Check availability on Chester Family Hotels

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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.
CA $140
CA $172 total
includes taxes & fees
Oct 12 - Oct 13
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 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.
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
CA $306
CA $347 total
includes taxes & fees
Oct 8 - Oct 9
The Dominion House Bed & Breakfast
A wooden deck with outdoor furniture, a pool, and a lush garden.
An aerial view of a large, two-story house surrounded by dense forest, with a swimming pool and outdoor seating area.
A wooden staircase with a chandelier, white railings, and a glass door with a geometric pattern.
A deck with outdoor seating, a hot tub, and a swimming pool surrounded by greenery.

3. Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub
Chester
CA $2,656
CA $4,563 total
includes taxes & fees
Oct 18 - Oct 19
Serene 10BR Retreat w/Pool, Gym & Hot Tub
A hotel entrance with stone pillars, a covered walkway, and a bench.
A hotel room with a bed, a sofa, a desk, and a large window with curtains.
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.

4. Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury
Monroe
CA $156
CA $177 total
includes taxes & fees
Oct 28 - Oct 29
Sleep Inn & Suites Monroe - Woodbury
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 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.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
CA $161
CA $190 total
includes taxes & fees
Nov 3 - Nov 4
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 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.

6. Tru by Hilton Middletown

Tru by Hilton Middletown
Middletown
CA $116
CA $137 total
includes taxes & fees
Nov 1 - Nov 2
Tru 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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
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.
CA $184
CA $226 total
includes taxes & fees
Nov 1 - Nov 2
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.
A hotel entrance with a covered area, a sign reading "Hampton Inn," and a clear sky.
An outdoor patio with brick flooring, round tables, and blue umbrellas.

8. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.
CA $168
CA $207 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn Harriman Woodbury
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 restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.

9. 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 $154
CA $369 total
includes taxes & fees
Oct 25 - Oct 26
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.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
CA $164
CA $194 total
includes taxes & fees
Nov 4 - Nov 5
Holiday Inn Express & Suites Middletown - Goshen by IHG
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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Very accommodating staff, they were able to move me to a room that didn't require stairs because I had a rolling cart with gear I needed to bring inside each night. I had to add a night to my reservation, so I bought another night there on Hotels.com, and they simply kept me in my same room so I didn't need to move anything. It was great! Good coffee available in the morning, easy location to get in and out of. They were actively renovating the property while I was there, so I don't count that towards the cleanliness of the property; everything was very clean, even while under renovation. Will stay again when needed!"
Brian 1-night trip
Posted 16 hours ago
Ramada by Wyndham Newburgh/West Point
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Cute little inn! Rooms were clean however they need a little TLC. My friend complained of hearing the train horns during the night, but I slept right through it! The coffee machine in the lobby—the only coffee machine—was out of order."
Tracy 1-night trip
Posted 23 hours 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 2 days ago
Studio 6 Extended Stay Fishkill Westage Center NY
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 7 days ago
Sonesta Simply Suites 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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