Hotels with Swimming Pool in Chester, New York

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Check availability on Chester Hotels with Swimming 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 P6,151
P7,266 total
includes taxes & fees
Feb 19 - Feb 20
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 P12,476
P14,114 total
includes taxes & fees
Feb 16 - Feb 17
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, (1,001 reviews)
"Love staying here "
United States
devin
The price is P4,883
P5,768 total
includes taxes & fees
Feb 22 - Feb 23
Courtyard by Marriott Middletown Goshen
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, (973 reviews)
"Room was clean & comfortable. Staff was accommodating and friendly."
United States
Nadine
The price is P6,412
P7,574 total
includes taxes & fees
Mar 5 - Mar 6
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 P6,905
P7,812 total
includes taxes & fees
Feb 16 - Feb 17
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 P5,397
P6,645 total
includes taxes & fees
Feb 22 - Feb 23
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, (1,003 reviews)
"Clean room, friendly staff"
United States
KAREN
The price is P5,570
P6,301 total
includes taxes & fees
Feb 15 - Feb 16
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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)
"Room clean, staff friendly"
United States
KATHRYN
The price is P4,883
P5,768 total
includes taxes & fees
Feb 23 - Feb 24
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, (1,001 reviews)
"Room was beautifully spotless. Enjoyed everything during my stay."
United States
Francine
The price is P5,662
P6,406 total
includes taxes & fees
Feb 23 - Feb 24
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 P4,961
P5,607 total
includes taxes & fees
Feb 22 - Feb 23
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

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"The front desk personnel were very nice and efficient. The room was clean and the bed was comfortable. "
CATHERINE 1-night trip
Posted 4 days ago
DoubleTree by Hilton Hotel Nanuet

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.

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