The Best Hotels with a Pool in Chester, NY from NT$4,241 in 2026

Q: 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. Spark by Hilton Fishkill : Provides continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen : Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Overlook Lodge at Bear Mountain : Features a snack bar/deli, a pool, and free self parking. Crowne Plaza Suffern - Mahwah by IHG : Hotel steps from LEGOLAND® New York. Features full, a seasonal outdoor pool, and complimentary wireless 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.

NT$4,241 total

includes taxes & fees

Aug 16 - Aug 17

The Dominion House Bed & Breakfast

Chester

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

NT$7,851 total

includes taxes & fees

Jul 27 - Jul 28

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

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

NT$5,723 total

includes taxes & fees

Aug 12 - Aug 13

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.

NT$4,681 total

includes taxes & fees

Aug 16 - Aug 17

Sleep Inn & Suites Middletown - Goshen

Middletown

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

NT$4,673 total

includes taxes & fees

Aug 12 - Aug 13

Hampton Inn Harriman Woodbury

Central Valley

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

NT$5,465 total

includes taxes & fees

Aug 2 - Aug 3

Holiday Inn Express & Suites Middletown - Goshen by IHG

Middletown

Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.

NT$4,423 total

includes taxes & fees

Aug 23 - Aug 24

Courtyard by Marriott Middletown Goshen

Middletown

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

NT$4,356 total

includes taxes & fees

Aug 25 - Aug 26

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Choose what matters most at hotels with a pool in Chester

Breakfast included

Hot tub

Top Chester Hotel Reviews

Mountain Creek

8/10 Good

"The comforter in our room was disgusting. It had numerous visible stains that looked like old blood stains. Even though they appeared to have been washed, the stains were still very noticeable. A comforter in this condition should not be used for guests. The hotel should replace it immediately. Clean bedding is one of the most basic standards of any hotel, and this was completely unacceptable. I sincerely hope the hotel will take this issue seriously and replace all worn or heavily stained comforters to ensure a clean and comfortable stay for future guest"

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. Spark by Hilton Fishkill: Provides continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Overlook Lodge at Bear Mountain: Features a snack bar/deli, a pool, and free self parking. Crowne Plaza Suffern - Mahwah by IHG: Hotel steps from LEGOLAND® New York. Features full, a seasonal outdoor pool, and complimentary wireless internet access.

What is there to see and do in Chester?

Explore places like LEGOLAND® New York and Woodbury Common Premium Outlets 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.

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Our top choices for Chester hotels with a pool