TOP Hotels with 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. DoubleTree by Hilton Hotel Nanuet : Offers a snack bar/deli, a pool and free self parking. Sonesta Simply Suites Nanuet : Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Sleep Inn & Suites Middletown - Goshen : Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn & Suites Mahwah : Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers daily, an indoor 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.

฿4,622 total

includes taxes & fees

12 Apr - 13 Apr

The Dominion House Bed & Breakfast

Chester

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

฿7,800 total

includes taxes & fees

23 Apr - 24 Apr

Overlook Lodge at Bear Mountain

Bear Mountain

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

฿4,699 total

includes taxes & fees

12 Apr - 13 Apr

Courtyard by Marriott Middletown Goshen

Middletown

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

฿3,832 total

includes taxes & fees

29 Apr - 30 Apr

Hampton Inn by Hilton Middletown

Middletown

Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.

฿3,500 total

includes taxes & fees

20 Apr - 21 Apr

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

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

฿4,361 total

includes taxes & fees

22 Apr - 23 Apr

Sleep Inn & Suites Middletown - Goshen

Middletown

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

฿4,159 total

includes taxes & fees

13 Apr - 14 Apr

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

New Windsor

Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.

฿3,395 total

includes taxes & fees

10 May - 11 May

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Choose what matters most at hotels with a pool in Chester

Breakfast included

Hot tub

Top Chester Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"nice experience overall satisfied "

Courtyard by Marriott Newburgh Stewart Airport

4/10 Poor

"The housekeeping ladies were lovely and very helpful. Especially one lady in particular, older spanish lady. The hotel feels outdated for the price. There isnt any A.C in the room and the window only cracked a little. The pillows are thin and terrible and the bed felt "off". The lady on check-in day was less than a delight to put it nicely, we were also given the wrong room but there was no telling her that. How do you expect 4 peopls to sleep in a king size bed comfortably for 4 days? And then to get a microwave was a joke "come down to lobby yiou can use the one down here" WHY DO I HAVE TO BEG FOR A MICROWAVE?!?!? The "spa" is STILL out of commission despite it being listed as an available amenity. This was our second stay and honestly probably the last. Almost 600 i paid and have beg for a microwave and get treated like crap? Fire all the daytime concierge. "

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: Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Sleep Inn & Suites Middletown - Goshen: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hampton Inn & Suites Mahwah: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers daily, an indoor pool and complimentary high-speed (wired) Internet access.

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 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 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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