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 $159

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Check availability on Chester Family Hotels

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Chester family-friendly hotels

Exterior
Superior Double Room, Ensuite (Primrose) | Miscellaneous
Miscellaneous
Miscellaneous

1. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
CA $297
CA $337 total
includes taxes & fees
Sep 28 - Sep 29
The Dominion House Bed & Breakfast
Pool
Exterior
Outdoor spa tub
Private kitchen

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

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
CA $3,359
CA $5,278 total
includes taxes & fees
Sep 27 - Sep 28
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Reception
Terrace/patio
View from property
Restaurant

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.
CA $172
CA $212 total
includes taxes & fees
Sep 13 - Sep 14
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby
Room
Exterior
Fitness facility

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.
CA $135
CA $159 total
includes taxes & fees
Sep 30 - Oct 1
Hampton Inn by Hilton Middletown
Property amenity
Lobby
Exterior
Property amenity

5. 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 $152
CA $179 total
includes taxes & fees
Sep 21 - Sep 22
Courtyard by Marriott Middletown Goshen
Pool
Lobby
Ninjago Premium Themed
Lobby

6. 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 $289
CA $523 total
includes taxes & fees
Oct 4 - Oct 5
LEGOLAND Hotel NEW York
Lobby
Lobby
Exterior
Suite, Multiple Beds, Non Smoking

7. Comfort Suites Central Valley - Woodbury

Comfort Suites Central Valley - Woodbury
Central Valley
CA $159
CA $196 total
includes taxes & fees
Sep 21 - Sep 22
Comfort Suites Central Valley - Woodbury
Exterior
Lobby
Fitness facility
Room

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
CA $183
CA $217 total
includes taxes & fees
Sep 20 - Sep 21
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Business centre
Bathroom
Room, 2 Double Beds, Non Smoking
Lobby

9. 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 cozy rooms at this budget-friendly motel near Woodbury outlets.
CA $135
CA $167 total
includes taxes & fees
Sep 20 - Sep 21
Americas Best Value Inn at Central Valley-Woodbury
Exterior detail
Exterior detail
Interior detail
Lobby sitting area

10. Borland House Inn

Borland House Inn
Montgomery
CA $142
CA $173 total
includes taxes & fees
Sep 13 - Sep 14
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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"This location and its history made this Inn a great stopover night for us as we travelled down the East Coast. The scenery is beautiful and the staff are helpful and friendly. This would would be a great place to meet with family members and/or friends to enjoy sharing a cottage (with 6 rooms and a common area) to enjoy a few nights or week together. There is a lot to do in the area and the porch of the cottage lends itself to just sitting and admiring the natural surroundings, especially the lake!"
Nancy 1-night trip
Posted 1 hour ago
Overlook Lodge at Bear Mountain
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"rooms spacious and clean .. absolutely love that I got a text message to see if we needed anything and if they could help at all- never got that from a hotel before However, there was nobody there when we checked out at 5:30 AM at the front desk.. wanted to ask him a question but I didn’t get to. Like to also that they had a bag with some breakfast food for us to take on the road before kitchen open"
Cathy 1-night trip
Posted 2 hours ago
Hampton Inn & Suites Mahwah
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

10/10 Excellent
"Everything was close and breakfast is good"
Carlos 1-night trip
Posted 5 hours ago
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Very friendly and clean, very nice view of the river would recommend room with balcony on 2nd floor for the nice view"
Ryan 1-night trip
Posted 15 hours ago
Inn on the Hudson
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

10/10 Excellent
"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."
Adrienne 1-night trip
Posted 4 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

10/10 Excellent
"Very good."
Ibrahim 1-night trip
Posted 5 days ago
Courtyard by Marriott Mahwah

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 Gateway Plaza Shopping Center and Galleria at Crystal Run.

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