Find Hotels with a Pool in Chester, NY

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Top 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, (1008)
"The staff was excellent "
United States
Kelley
$104 nightly
The price is $123
Dec 10 - Dec 11
Total with taxes and fees
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)
"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
$215 nightly
The price is $243
Dec 15 - Dec 16
Total with taxes and fees
The Dominion House Bed & Breakfast
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We loved everything from the staff to the stay "
United States
Arnassia
$294 nightly
The price is $346
Dec 22 - Dec 23
Total with taxes and fees
LEGOLAND Hotel NEW York
BBQ/picnic area
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
$75 nightly
The price is $89
Dec 21 - Dec 22
Total with taxes and fees
Hampton Inn by Hilton Middletown
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, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$102 nightly
The price is $116
Dec 10 - Dec 11
Total with taxes and fees
Overlook Lodge at Bear Mountain
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
8.6 out of 10, Excellent, (1004)
"Brayden was great"
United States
Will
$92 nightly
The price is $104
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hilton Garden Inn Fishkill
Indoor pool
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, (1009)
"I had a very nice stay"
United States
Mischelle
$95 nightly
The price is $107
Jan 9 - Jan 10, 2026
Total with taxes and fees
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Seasonal outdoor pool
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
Goshen
8.8 out of 10, Excellent, (1003)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
$97 nightly
The price is $119
Dec 24 - Dec 25
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Seasonal outdoor pool
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

2.0 star property
Wurtsboro
7.6 out of 10, Good, (591)
"I love "
United States
Niralkumar
$94 nightly
The price is $106
Jan 2 - Jan 3, 2026
Total with taxes and fees
Days Inn by Wyndham Wurtsboro
Indoor pool
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, (932)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
$117 nightly
The price is $139
Jan 4 - Jan 5, 2026
Total with taxes and fees
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

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Clean room, helpful staff, great breakfast. Will stay with Hampton Inn and Suites again."
Lisa 1-night trip
Posted 1 day ago
Hampton Inn & Suites Mahwah

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. Sonesta Simply Suites Nanuet: Provides a snack bar/deli, a pool, and free self parking. DoubleTree by Hilton Hotel Nanuet: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Overlook Lodge at Bear Mountain: Offers full, a pool, and complimentary wired internet access. Hampton Inn & Suites Mahwah: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access.
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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