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. Sleep Inn & Suites Middletown - Goshen : Provides continental, an indoor pool and complimentary high-speed (wired) Internet access. Crowne Plaza Suffern - Mahwah by IHG : Offers buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen : Offers a snack bar/deli, an indoor pool and buffet.

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Our top choices for Chester hotels with a pool

A Simon Premium Outlet sign at Woodbury Commons.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

Rp2.545.473 total

includes taxes & fees

22 Nov - 23 Nov

A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

2. The Dominion House Bed & Breakfast

Chester

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

Rp2.207.951 total

includes taxes & fees

9 Nov - 10 Nov

A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.

3. Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

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

Rp2.880.403 total

includes taxes & fees

4 Nov - 5 Nov

A swimming pool with colorful umbrellas and lounge chairs.

4. LEGOLAND Hotel NEW York

Goshen

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

Rp5.102.891 total

includes taxes & fees

1 Nov - 2 Nov

An indoor swimming pool with clear blue water, surrounded by tiled flooring and furnished with chairs and tables.

5. Hampton Inn Harriman Woodbury

Central Valley

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

Rp2.638.140 total

includes taxes & fees

15 Nov - 16 Nov

An indoor swimming pool with clear water, surrounded by walls with a blue and white color scheme, and equipped with safety railings and seating areas.

6. 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.

Rp2.348.921 total

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with blue tiles, a diving board, and several chairs.

7. 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.

Rp2.613.480 total

includes taxes & fees

8 Nov - 9 Nov

An indoor swimming pool with lounge chairs and a stone wall.

8. Sleep Inn & Suites Middletown - Goshen

Middletown

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

Rp2.166.832 total

includes taxes & fees

18 Nov - 19 Nov

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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

8/10 Good

"Great place, but was super crowded."

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. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool and complimentary high-speed (wired) Internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers buffet, an indoor pool and free self parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Offers a snack bar/deli, an indoor pool and buffet.

What is there to see and do in Chester?

Explore places such as 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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