Find Hotels with a Pool in Chester, NY

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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, (1,000 reviews)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is NT$2,847
NT$3,363 total
includes taxes & fees
Jan 22 - Jan 23
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 reviews)
"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 NT$6,802
NT$7,694 total
includes taxes & fees
Jan 20 - Jan 21
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
9.0 out of 10, Wonderful, (1,028 reviews)
"Nice clean hotel with friendly staff. "
United States
michelle
The price is NT$2,983
NT$3,472 total
includes taxes & fees
Feb 1 - Feb 2
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, (1,000 reviews)
"Clean Rooms, clean hotel overall. Plenty of parking."
United States
KenNETH
The price is NT$2,635
NT$3,113 total
includes taxes & fees
Jan 20 - Jan 21
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, (1,000 reviews)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is NT$3,101
NT$3,585 total
includes taxes & fees
Jan 23 - Jan 24
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, (1,004 reviews)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is NT$3,765
NT$4,259 total
includes taxes & fees
Jan 15 - Jan 16
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, (1,015 reviews)
"everything was great "
United States
Christopher
The price is NT$2,899
NT$3,279 total
includes taxes & fees
Feb 1 - Feb 2
Hilton Garden Inn Fishkill
Indoor pool
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,012 reviews)
"Love staying here "
United States
devin
The price is NT$2,931
NT$3,462 total
includes taxes & fees
Jan 22 - Jan 23
Courtyard by Marriott Middletown Goshen
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,022 reviews)
"Superb place to stay."
United States
Denessy
The price is NT$3,132
NT$3,543 total
includes taxes & fees
Jan 15 - Jan 16
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Outdoor spa tub
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (954 reviews)
"GREAT STAY, CLEAN HOTEL AND ROOM, GREAT POOL AND HOT TUB GYM IS CLEAN LOVED IT"
United States
NICOLE
The price is NT$3,281
NT$3,876 total
includes taxes & fees
Jan 18 - Jan 19
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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.
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Top Chester Hotel Reviews

Mountain Creek

Mountain Creek

10/10 Excellent
"easy check-in/check-out"
Taline 1-night trip
Posted 2 days ago
Mountain Creek

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: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers continental, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Mahwah: Provides 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.

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