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, (1,001 reviews)
"great stay. had everything needed. "
United States
Dana
The price is SAR 379
SAR 447 total
includes taxes & fees
22 Feb - 23 Feb
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 SAR 806
SAR 912 total
includes taxes & fees
16 Feb - 17 Feb
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, (1,004 reviews)
"Love staying here "
United States
devin
The price is SAR 316
SAR 373 total
includes taxes & fees
17 Feb - 18 Feb
Courtyard by Marriott Middletown Goshen
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, (973 reviews)
"Room was clean & comfortable. Staff was accommodating and friendly."
United States
Nadine
The price is SAR 383
SAR 452 total
includes taxes & fees
17 Feb - 18 Feb
La Quinta Inn & Suites by Wyndham 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, (1,001 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 SAR 375
SAR 424 total
includes taxes & fees
18 Feb - 19 Feb
Overlook Lodge at Bear Mountain
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, (1,003 reviews)
"Was nice place to stay I like it "
United States
Artemio
The price is SAR 349
SAR 429 total
includes taxes & fees
19 Feb - 20 Feb
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, (1,011 reviews)
"Clean room, friendly staff"
United States
KAREN
The price is SAR 360
SAR 407 total
includes taxes & fees
15 Feb - 16 Feb
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Seasonal outdoor pool

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"Room clean, staff friendly"
United States
KATHRYN
The price is SAR 303
SAR 358 total
includes taxes & fees
26 Feb - 27 Feb
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, (1,004 reviews)
"Room was beautifully spotless. Enjoyed everything during my stay."
United States
Francine
The price is SAR 366
SAR 414 total
includes taxes & fees
19 Feb - 20 Feb
Hilton Garden Inn Fishkill
Seasonal outdoor pool

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (610 reviews)
"Excellent, clean, comfortable stay on a stormy night. Great staff."
United States
Paul
The price is SAR 338
SAR 381 total
includes taxes & fees
22 Feb - 23 Feb
Days Inn by Wyndham Wurtsboro
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

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Top Chester Hotel Reviews

Residence Inn by Marriott Saddle River

Residence Inn by Marriott Saddle River

10/10 Excellent
"Xxxxx"
Dominick L 1-night trip
Posted 3 weeks ago
Residence Inn by Marriott Saddle River
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"Stay was great. Hotel was very nice, room was good and the staff was awesome. Breakfast was good also, with a good variety."
Keisha 1-night trip
Posted 1 month 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. DoubleTree by Hilton Hotel Nanuet: Offers a snack bar/deli, a pool, and free self parking. Crowne Plaza Suffern - Mahwah by IHG: Features a water park, an outdoor pool, and a sauna. Mountain Creek: Features daily, an indoor pool, and free self parking. Sonesta Simply Suites Nanuet: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers 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 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.