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. 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. Spark by Hilton Fishkill : Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Sleep Inn & Suites Middletown - Goshen : Offers a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet : Offers daily, an indoor pool and free self parking.

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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.

฿4,162 total

includes taxes & fees

12 Jul - 13 Jul

The Dominion House Bed & Breakfast

Chester

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

฿8,114 total

includes taxes & fees

22 Jul - 23 Jul

Seasonal outdoor pool, pool umbrellas, pool loungers

LEGOLAND Hotel NEW York

Goshen

Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.

฿15,306 total

includes taxes & fees

12 Jul - 13 Jul

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

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

฿5,915 total

includes taxes & fees

22 Jul - 23 Jul

Days Inn by Wyndham Wurtsboro

Wurtsboro

Take a dip in the seasonal outdoor pool, a refreshing retreat with mountain views.

฿4,221 total

includes taxes & fees

16 Jul - 17 Jul

Hampton Inn Harriman Woodbury

Central Valley

Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.

฿5,363 total

includes taxes & fees

22 Jul - 23 Jul

Holiday Inn Express Haskell - Wayne Area by IHG

Wanaque

Discover a lakeside splash zone where kids make friends at this clean, modern retreat.

฿5,013 total

includes taxes & fees

23 Jul - 24 Jul

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.

฿4,859 total

includes taxes & fees

26 Jul - 27 Jul

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Choose what matters most at hotels with a pool in Chester

Breakfast included

Hot tub

Top Chester Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

"Friendly atmosphere and staff. Lots to see and do! A bit outdated so must be ok with a outdoorsy/rustic feel."

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent

"The woman at the front desk was incredibly friendly, polite and helpful. I was sad to see that she appears to be so short staffed that I saw her trying to manage different areas at different times. The room was clean and comfortable. The pool was a bit ‘cloudy’ so maybe increasing the frequency of the cleaning protocols would be helpful."

Days Inn by Wyndham Nanuet / Spring Valley

8/10 Good

"Room was very clean and looked like it was remodeld. The gentlemen at checkin was polite and friendly. It is a continental breakfast, that is located in the small checkin room. One has to sit on a high stool to put their food on the counter. Air Conditioning not working that day in that room. The parking is good."

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. 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. Spark by Hilton Fishkill: Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Sleep Inn & Suites Middletown - Goshen: Offers a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet: Offers daily, an indoor pool and free self parking.

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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