TOP Hotels with Swimming Pool in Chester, NY for 2026

Q: 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. Spark by Hilton Fishkill : Provides a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet : Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Studio 6 Extended Stay Fishkill Route 9 NY : Features daily, an indoor pool and free self parking. Sonesta Simply Suites Nanuet : Offers buffet, a pool and complimentary high-speed (wired) Internet access.

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Our top choices for Chester hotels with a pool

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.

₹15,107 total

includes taxes & fees

15 Jun - 16 Jun

The Dominion House Bed & Breakfast

Chester

Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.

₹23,133 total

includes taxes & fees

16 Jun - 17 Jun

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.

₹16,863 total

includes taxes & fees

16 Jun - 17 Jun

La Quinta Inn & Suites by Wyndham Middletown-Goshen

Middletown

Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.

₹15,066 total

includes taxes & fees

21 Jun - 22 Jun

Sleep Inn & Suites Middletown - Goshen

Middletown

Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.

₹13,769 total

includes taxes & fees

18 Jun - 19 Jun

Overlook Lodge at Bear Mountain

Bear Mountain

Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.

₹17,416 total

includes taxes & fees

15 Jun - 16 Jun

Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Splash into year-round relaxation at this hotel's indoor swimming oasis, just minutes from Algonquin Park and local attractions.

₹13,727 total

includes taxes & fees

21 Jun - 22 Jun

Courtyard by Marriott Middletown Goshen

Middletown

Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.

₹13,274 total

includes taxes & fees

21 Jun - 22 Jun

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Choose what matters most at hotels with a pool in Chester

Breakfast included

Hot tub

Top Chester Hotel Reviews

Studio 6 Extended Stay Fishkill Route 9 NY

10/10 Excellent

"Room was clean."

The Crossroads Hotel, Newburgh

2/10 Terrible

"Worst hotel stay ever … you can skip this one. A few bright notes: evening receptionist was accommodating and a pleasure to work with; external grounds were immaculate with plenty of parking; entrance lobby was clean and inviting. The three rooms I looked at were clean but smelled funky. All had interior damage. (One had blood spatter on the pulldown shade!) The third room (cleanest smell) had a damaged shower curtain rod, no official room label (hand-written on the wall) and the door didn’t close properly (One had to push it shut!) On the second/third floors, the smell of cigarettes and smoked meth emanating from several rooms, with uncollected trash left outside individual doors. I took a shower and slept in my vehicle."

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. Spark by Hilton Fishkill: Provides a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Studio 6 Extended Stay Fishkill Route 9 NY: Features daily, an indoor pool and free self parking. Sonesta Simply Suites Nanuet: Offers buffet, a pool and complimentary high-speed (wired) Internet access.

What is there to see and do in Chester?

Explore places such as LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions such as 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 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.

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