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Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Next weekend
Jul 3 - Jul 5
In two weeks
Jul 10 - Jul 12

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)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
The price is ￥20,703
￥25,492 total
includes taxes & fees
Jul 2 - Jul 3
Holiday Inn Express Hotel & Suites Chester by IHG
Outdoor pool, sun loungers

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
  • cleanliness
    Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
The price is ￥34,774
￥39,338 total
includes taxes & fees
Jun 30 - Jul 1
The Dominion House Bed & Breakfast
Outdoor pool

11BR Retreat w Pool & Game Room

11BR Retreat w Pool & Game Room
Chester
The price is ￥394,581
￥621,814 total
includes taxes & fees
Jul 1 - Jul 2
11BR Retreat w Pool & Game Room
Seasonal outdoor pool, cabanas (surcharge), pool umbrellas

Jellystone Park Gardiner

Jellystone Park Gardiner
3.0 star property
Gardiner
The price is ￥57,620
￥64,535 total
includes taxes & fees
Jul 9 - Jul 10
Jellystone Park Gardiner
Indoor pool, sun loungers

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (730 reviews)
  • cleanliness
    Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.
The price is ￥19,085
￥22,544 total
includes taxes & fees
Jul 26 - Jul 27
Holiday Inn Express & Suites Middletown - Goshen by IHG
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, (1,003 reviews)
  • cleanliness
    Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.
The price is ￥19,797
￥23,386 total
includes taxes & fees
Jul 26 - Jul 27
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, (1,004 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
The price is ￥21,813
￥26,858 total
includes taxes & fees
Jul 2 - Jul 3
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
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
The price is ￥23,291
￥28,678 total
includes taxes & fees
Jul 19 - Jul 20
Fairfield Inn & Suites by Marriott Goshen Middletown
Reception

Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
2.5 star property
Newburgh
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splash into year-round relaxation at this hotel's indoor swimming oasis, just minutes from Algonquin Park and local attractions.
The price is ￥19,761
￥23,343 total
includes taxes & fees
Jul 12 - Jul 13
Hampton Inn & Suites Newburgh Stewart Airport
Indoor pool

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,042 reviews)
  • cleanliness
    Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
The price is ￥20,282
￥23,958 total
includes taxes & fees
Jul 26 - Jul 27
Sleep Inn & Suites 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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Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub

Top Chester Hotel Reviews

Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

8/10 Good
"We rented a suite with 2 queen beds and a sofa bed. There were 3 people in our party staying for 4 days. There was no dresser only one drawer in the cabinet which had TV on top. Management said the floor we were on had just been renovated. The design person should have included a dresser. Also our toilet leaked for the first few days. Mgmt said the water company was there to fix some items. The bathtub / shower was not renovated so that should be replaced. The front desk and staff were very accommodating and a pleasure to work with."
Kathleen 4-night trip
Posted 6 hours 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. Overlook Lodge at Bear Mountain: Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool, and complimentary wired internet access. DoubleTree by Hilton Hotel Nanuet: Features a snack bar/deli, a pool, and free self parking. Crowne Plaza Suffern - Mahwah by IHG: Features free self parking, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Chester?
Explore places like LEGOLAND® New York while you're in the area. Make a point to visit attractions like The Rock Sports Complex and Castle Fun Center. 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.