Hotels with Swimming Pool in Chester, New York

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Our top choices for Chester hotels with a pool

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, (1002)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is P7,353
P8,686 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Holiday Inn Express Hotel & Suites Chester by IHG

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 P12,647
P14,307 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Dominion House Bed & Breakfast

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 P11,201
P20,382 total
includes taxes & fees
Jan 2 - Jan 3, 2026
LEGOLAND Hotel NEW York

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Room was clean and staff was great!"
United States
Annemarie
The price is P4,600
P5,434 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn by Hilton Middletown

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (599)
"Excellent, clean, comfortable stay on a stormy night. Great staff."
United States
Paul
The price is P5,824
P6,581 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Days Inn by Wyndham Wurtsboro

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, (1000)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is P5,294
P5,989 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1016)
"Clean room, staff was very nice."
United States
Jonathan
The price is P6,029
P7,017 total
includes taxes & fees
Jan 11 - Jan 12, 2026
DoubleTree by Hilton Hotel Nanuet

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, (1006)
"Superb place to stay."
United States
Denessy
The price is P5,347
P6,048 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1006)
"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 P7,000
P7,919 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Overlook Lodge at Bear Mountain

Courtyard by Marriott Fishkill

Courtyard by Marriott Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (734)
"Great Stay!"
United States
Les
The price is P6,450
P7,297 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Courtyard 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.

Top Chester Hotel Reviews

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 a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Hampton Inn & Suites Mahwah: Provides daily, a seasonal outdoor 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 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.

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