The Best Family Hotels in Chester, NY from ￥12,033 in 2026

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Our top choices for Chester family-friendly hotels

A Holiday Inn Express hotel with a covered entrance, a parking lot, and a well-lit facade.

1. 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 Center.

￥18,913 total

includes taxes & fees

Nov 15 - Nov 16

A large, two-story white house with a wrap-around porch and a small front garden.

2. The Dominion House Bed & Breakfast

Chester

￥19,257 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a bed, a nightstand, a bench, a window, and a ceiling fan.

3. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Chester

￥118,320 total

includes taxes & fees

Nov 8 - Nov 9

A hotel entrance with stone pillars, a covered walkway, and a bench.

4. Sleep Inn & Suites Monroe - Woodbury

Monroe

￥18,952 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with colorful umbrellas and lounge chairs.

5. 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.

￥34,840 total

includes taxes & fees

Nov 13 - Nov 14

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.

6. 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.

￥25,014 total

includes taxes & fees

Nov 8 - Nov 9

A lobby with a fireplace, seating area, and a reception desk.

7. Hampton Inn Harriman Woodbury

Central Valley

Family fun with indoor pool and entertainment near Woodbury Common Premium Outlets.

￥22,908 total

includes taxes & fees

Nov 22 - Nov 23

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

Middletown

￥21,032 total

includes taxes & fees

Nov 22 - Nov 23

A modern indoor space with two foosball tables, comfortable seating, and a TV screen.

9. Tru by Hilton Middletown

Middletown

￥16,501 total

includes taxes & fees

Nov 29 - Nov 30

A hotel with a modern facade, multiple floors, and a covered entrance area.

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

Middletown

￥16,647 total

includes taxes & fees

Dec 6 - Dec 7

View all properties

Choose what matters most at family-friendly hotels in Chester

Breakfast included

Pool

Top Chester Hotel Reviews

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

10/10 Excellent

jonathan

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

10/10 Excellent

Jordan

A large, two-story house with a wrap-around porch and multiple chimneys.

Parkway House Goshen Family-Friendly Bed & Breakfast

Goshen

10/10 Excellent

Crystal

A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

Sleep Inn & Suites Middletown - Goshen

Middletown

10/10 Excellent

Damion

Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

10/10 Excellent

Kathleen

Tru by Hilton Middletown

Middletown

10/10 Excellent

Love coming to this hotel, it has a wonderful atmosphere, caring staff and the environment is throughly clean and friendly. Saxida is very lovley and accommodating she definitely cares about the guests that come in and any problems that may occur she is urgent to fix it I appreciate how she remembered who I was and her energy is full of light. I appreciate everything this hotel has to offer and will be returning to make more fun memories in the future!

Daniela

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

Residence Inn by Marriott Middletown Goshen

Middletown

10/10 Excellent

Everything was beautiful, it looks like a new property. My only complaint was after shutting off the air conditioner/heater it still remained on and was very noisy keeping my wife and I up most of the night. Even switching the circuit breaker off didn’t solve the problem. I’m not one to complain though and didn’t bother the staff at the late hour. I still wouldn’t hesitate to stay at a residence inn property in the future.

Joseph

An outdoor patio area with seating, a fire feature, and a view of the surrounding buildings.

Home2 Suites by Hilton Middletown

Middletown

10/10 Excellent

Anonymous traveler

A buffet with various food items, including omelets and baked goods, served in metal trays.

Holiday Inn Express & Suites Montgomery by IHG

Montgomery

10/10 Excellent

Marissa

A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.

Homewood Suites Stewart Airport

New Windsor

10/10 Excellent

Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.

Anonymous traveler

A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

Candlewood Suites Middletown Goshen by IHG

Middletown

10/10 Excellent

Moraivic

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

Hampton Inn by Hilton Middletown

Middletown

10/10 Excellent

Destiny

A buffet with various food items, including omelets and baked goods, served in metal containers.

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

10/10 Excellent

David Allen

A hotel room with a green sofa, a small table, a bed with a headboard, a desk with a lamp, and a framed picture on the wall.

Quality Inn & Suites Fishkill South near I-84

Fishkill

10/10 Excellent

Lynn

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.

Find Family Hotels in Chester, NY

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester family-friendly hotels

1. Holiday Inn Express Hotel & Suites Chester by IHG

2. The Dominion House Bed & Breakfast

3. Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

4. Sleep Inn & Suites Monroe - Woodbury

5. LEGOLAND Hotel NEW York

6. Fairfield Inn & Suites by Marriott Goshen Middletown

7. Hampton Inn Harriman Woodbury

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

9. Tru by Hilton Middletown

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

Choose what matters most at family-friendly hotels in Chester

Top Chester Hotel Reviews

Fairfield Inn & Suites by Marriott Goshen Middletown

10/10 Excellent

Frequently Asked Questions

What's Chester like for family-friendly vacations?

What's the best place to stay for a family vacation in Chester?

When’s the best time to book a family-friendly vacation in Chester?

What's there to see and do with your family in Chester?