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Find Family Hotels in Chester, NY

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Check availability on Chester Family Hotels

Tonight
24 Sep - 25 Sep
Tomorrow
25 Sep - 26 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Chester family-friendly hotels

Exterior
Outdoor pool, sun loungers
Superior Double Room, Ensuite (Primrose) | Miscellaneous
Miscellaneous

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
AED 790
AED 893 total
includes taxes & fees
28 Sep - 29 Sep
The Dominion House Bed & Breakfast
Outdoor pool
Outdoor spa tub
Interior
Exterior

2. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
AED 7,275
AED 11,882 total
includes taxes & fees
27 Sep - 28 Sep
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Reception
Terrace/patio
Lobby
View from property

3. 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.
AED 474
AED 583 total
includes taxes & fees
4 Oct - 5 Oct
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby
Lobby
Fitness facility
Premium bedding, pillowtop beds, desk, laptop workspace

4. 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.
AED 374
AED 442 total
includes taxes & fees
6 Oct - 7 Oct
Hampton Inn by Hilton Middletown
Seasonal outdoor pool, pool umbrellas, sun loungers
Free daily full breakfast
Lobby
Lobby

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.
AED 741
AED 1,356 total
includes taxes & fees
4 Oct - 5 Oct
LEGOLAND Hotel NEW York
Property amenity
Lobby
Exterior
Property amenity

6. 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.
AED 387
AED 457 total
includes taxes & fees
12 Oct - 13 Oct
Courtyard by Marriott Middletown Goshen
Lobby
Free daily self-serve breakfast
Lobby
Exterior

7. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
AED 410
AED 504 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Suites Central Valley - Woodbury
Exterior
Premium bedding, pillowtop beds, desk, laptop workspace
Rainfall showerhead, free toiletries, hair dryer, towels
Fitness facility

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
AED 493
AED 582 total
includes taxes & fees
27 Sep - 28 Sep
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Free self parking
Terrace/patio
Meeting facility
Coffee/tea maker, fridge, microwave, dishwasher

9. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
AED 569
AED 685 total
includes taxes & fees
30 Sep - 1 Oct
Home2 Suites by Hilton Middletown
Hair dryer, towels
Reception
Exterior
Studio Suite, 1 King Bed, Non Smoking, Microwave | In-room safe, desk, laptop workspace, blackout drapes

10. Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown
Middletown
AED 290
AED 343 total
includes taxes & fees
27 Sep - 28 Sep
Super 8 by Wyndham 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

Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

10/10 Excellent
"All"
Jeanwoldy 1-night trip
Posted 17 hours ago
Hilton Garden Inn Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The property is a bit dated and its a bit odd to have to drive to the Inn to check in but it was mostly OK. Very rustic at the lodge and no staff onsite"
Dean 1-night trip
Posted 17 hours ago
Overlook Lodge at Bear Mountain
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"All great"
mahtab 1-night trip
Posted 2 days ago
Crowne Plaza Suffern - Mahwah by IHG
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Non"
bhaeldin 2-night trip
Posted 12 days ago
Ramada by Wyndham Newburgh/West Point

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.