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
2.5 star property
Chester
8.6 out of 10, Excellent, (1,000 reviews)
"Nice room breakfast was ok needs to be hot not judt luke warm."
United States
Donna
The price is ₩146,834
₩173,447 total
includes taxes & fees
Mar 22 - Mar 23
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous

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 ₩322,137
₩364,419 total
includes taxes & fees
Mar 18 - Mar 19
The Dominion House Bed & Breakfast
Indoor pool

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,002 reviews)
"Great stay!!! "
United States
diana
The price is ₩138,818
₩163,979 total
includes taxes & fees
Mar 22 - Mar 23
Courtyard by Marriott Middletown Goshen
Seasonal outdoor pool

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,005 reviews)
"Room was very clean"
United States
Patrick
The price is ₩178,299
₩201,703 total
includes taxes & fees
Mar 16 - Mar 17
Overlook Lodge at Bear Mountain
Seasonal outdoor pool

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (611 reviews)
"Clean spacious room, friendly staff."
United States
Dennis
The price is ₩133,499
₩150,849 total
includes taxes & fees
Mar 16 - Mar 17
Days Inn by Wyndham Wurtsboro
Seasonal outdoor pool

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,002 reviews)
"Nice staff, great room, wonderful breakfast "
United States
Brian
The price is ₩157,922
₩194,440 total
includes taxes & fees
Mar 22 - Mar 23
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool

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, (1,003 reviews)
"Superb place to stay."
United States
Denessy
The price is ₩133,484
₩150,984 total
includes taxes & fees
Mar 29 - Mar 30
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
BBQ/picnic area

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,002 reviews)
"Room clean, staff friendly"
United States
KATHRYN
The price is ₩134,998
₩159,467 total
includes taxes & fees
Mar 23 - Mar 24
Hampton Inn by Hilton Middletown
Indoor pool

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1,003 reviews)
"Room was beautifully spotless. Enjoyed everything during my stay."
United States
Francine
The price is ₩146,205
₩165,395 total
includes taxes & fees
Mar 23 - Mar 24
Hilton Garden Inn Fishkill
Indoor pool

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,005 reviews)
"Clean room very welcoming staff "
United States
Felicia
The price is ₩153,592
₩181,431 total
includes taxes & fees
Mar 24 - Mar 25
Sleep Inn & Suites 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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Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub

Top Chester Hotel Reviews

Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

10/10 Excellent
"Fantastic, clean, location, staff"
Gregory 4-night trip
Posted 3 hours ago
Courtyard by Marriott Newburgh Stewart Airport

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: Features continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. Hampton Inn & Suites Mahwah: Provides complimentary wired internet access, an indoor pool, and free self parking.
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 Museum Village and Goosepond Mountain State Park 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.