Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Tonight
8 Dec - 9 Dec
Tomorrow
9 Dec - 10 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

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, (1007)
"Great for a quick stay 👍"
United States
Jerry
The price is AED 342
AED 403 total
includes taxes & fees
11 Dec - 12 Dec
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
The price is AED 790
AED 893 total
includes taxes & fees
10 Dec - 11 Dec
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, (32)
"We loved everything from the staff to the stay "
United States
Arnassia
The price is AED 699
AED 1,272 total
includes taxes & fees
22 Dec - 23 Dec
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
The price is AED 276
AED 326 total
includes taxes & fees
21 Dec - 22 Dec
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
The price is AED 358
AED 405 total
includes taxes & fees
29 Dec - 30 Dec
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
The price is AED 337
AED 381 total
includes taxes & fees
4 Jan - 5 January 2026
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
The price is AED 404
AED 457 total
includes taxes & fees
21 Dec - 22 Dec
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)
"This place is fantastic from the staff to the rooms. Very clean. Will definitely stay here again."
United States
Linda
The price is AED 356
AED 439 total
includes taxes & fees
24 Dec - 25 Dec
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
The price is AED 345
AED 390 total
includes taxes & fees
2 Jan - 3 January 2026
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, (931)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
The price is AED 428
AED 505 total
includes taxes & fees
5 Jan - 6 January 2026
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 21 hours ago
Hampton Inn & Suites Mahwah

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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.