Chester Hotel Guide - Hotels with Pool in Chester, New York

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Check availability on Chester Hotels with Pool

Our top choices for Chester hotels with a pool

Indoor pool, pool 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)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is €91
includes taxes & fees
22 Jan - 23 Jan
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 €209
includes taxes & fees
19 Jan - 20 Jan
The Dominion House Bed & Breakfast
Indoor pool, open 8:30 AM to 9:30 PM, pool loungers

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,033 reviews)
"Nice clean hotel with friendly staff. "
United States
michelle
The price is €93
includes taxes & fees
1 Feb - 2 Feb
DoubleTree by Hilton Hotel Nanuet
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, (1,000 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 €116
includes taxes & fees
21 Jan - 22 Jan
Overlook Lodge at Bear Mountain
BBQ/picnic Area

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"Clean Rooms, clean hotel overall. Plenty of parking."
United States
KenNETH
The price is €82
includes taxes & fees
28 Jan - 29 Jan
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, (1,015 reviews)
"everything was great "
United States
Christopher
The price is €89
includes taxes & fees
1 Feb - 2 Feb
Hilton Garden Inn Fishkill
Outdoor spa tub

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, (956 reviews)
"GREAT STAY, CLEAN HOTEL AND ROOM, GREAT POOL AND HOT TUB GYM IS CLEAN LOVED IT"
United States
NICOLE
The price is €104
includes taxes & fees
1 Feb - 2 Feb
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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, (1,022 reviews)
"Superb place to stay."
United States
Denessy
The price is €96
includes taxes & fees
18 Jan - 19 Jan
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Indoor pool

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999 reviews)
"Yes stay was pleasant "
United States
henry
The price is €91
includes taxes & fees
23 Jan - 24 Jan
Comfort Suites Fishkill near Interstate 84
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, (1,001 reviews)
"Great place to stay when you’re in need of relaxation and some family time!"
United States
Cynthia
The price is €98
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Goshen Middletown
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 Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Clean and the staff are very nice "
Jeanette 1-night trip
Posted 2 days ago
Hampton Inn Harriman Woodbury

Frequently asked questions

What are some accommodation options 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 high-speed (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 high-speed (wired) Internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers continental, an indoor pool and complimentary high-speed (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 such as 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 consider a place to stay that has an outdoor pool if you plan to visit Chester in the hottest months of July, August or June, when the average temp is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 0°C.