Find Hotels with a Pool in Chester, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

Indoor pool, sun loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1008)
"The breakfast was a hit, the place is clean and I would stay here again."
United States
elizabeth
The price is ₩121,172
₩143,135 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is ₩315,738
₩357,180 total
includes taxes & fees
Dec 18 - Dec 19
The Dominion House Bed & Breakfast
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
8.8 out of 10, Excellent, (1008)
"Great staff, clean and the pool was awesome! "
Canada
Aleah
The price is ₩143,301
₩166,766 total
includes taxes & fees
Jan 4 - Jan 5, 2026
DoubleTree by Hilton Hotel Nanuet
BBQ/picnic area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1004)
"Room was clean and staff was great!"
United States
Annemarie
The price is ₩121,009
₩142,942 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hampton Inn by Hilton Middletown
Indoor pool
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very Good, (1001)
"Very nice stay."
United States
Peter
The price is ₩139,512
₩157,823 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1001)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is ₩174,757
₩197,696 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Overlook Lodge at Bear Mountain
Indoor pool
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1007)
"Brayden was great"
United States
Will
The price is ₩134,563
₩152,224 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Hilton Garden Inn Fishkill
Indoor pool
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1003)
"Yes stay was pleasant "
United States
henry
The price is ₩137,309
₩155,330 total
includes taxes & fees
Dec 30 - Dec 31
Comfort Suites Fishkill near Interstate 84
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is ₩279,524
₩508,636 total
includes taxes & fees
Dec 22 - Dec 23
LEGOLAND Hotel NEW York
Indoor pool
Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill

Residence Inn by Marriott Fishkill
3.0 star property
Fishkill
9.4 out of 10, Exceptional, (403)
"Excellent stay!"
United States
Margaret
The price is ₩193,922
₩219,374 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Residence Inn by Marriott Fishkill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"The breakfast was a hit, the place is clean and I would stay here again."
elizabeth 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Chester by IHG

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG: Hotel located near LEGOLAND® New York. Features on-the-go, a pool, and complimentary wired internet access. DoubleTree by Hilton Hotel Nanuet: Offers a snack bar/deli, a pool, and free self parking. Sonesta Simply Suites Nanuet: Offers full, a pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Mahwah: Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli.
What is there to see and do in Chester?
Make a point to visit attractions like The Rock Sports Complex and Castle Fun Center. Discover sights such as Goosepond Mountain State Park and Museum Village during your stay. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Chester in the warmest months of July, August, or June when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 32°F.