Hotels with Swimming Pool in Chester, New York

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Check prices for these dates

Tonight
Nov 13 - Nov 14
Tomorrow
Nov 14 - Nov 15
This weekend
Nov 13 - Nov 15
Next weekend
Nov 20 - Nov 22

Our top choices for Chester hotels with a pool

An indoor swimming pool with a 9-foot depth warning.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
The price is P6,895
P8,489 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Hotel & Suites Chester by IHG
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (241 reviews)
  • cleanliness
    Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
The price is P13,600
P15,385 total
includes taxes & fees
Nov 16 - Nov 17
The Dominion House Bed & Breakfast
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.

3. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
The price is P8,160
P10,047 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Goshen Middletown
An indoor swimming pool with clear blue water, surrounded by tiled flooring and furnished with chairs and tables.

4. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,152 reviews)
  • cleanliness
    Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
The price is P6,990
P8,606 total
includes taxes & fees
Dec 1 - Dec 2
Hampton Inn Harriman Woodbury
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

5. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (796 reviews)
  • cleanliness
    Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.
The price is P6,072
P7,173 total
includes taxes & fees
Dec 6 - Dec 7
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with colorful umbrellas and lounge chairs.

6. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.2 out of 10, Very good, (139 reviews)
  • cleanliness
    Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.
The price is P5,638
P14,944 total
includes taxes & fees
Nov 20 - Nov 21
LEGOLAND Hotel NEW York
A pool area with a hot tub, a pool lift, and safety signs on the walls.

7. La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,001 reviews)
  • cleanliness
    Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.
The price is P7,151
P8,447 total
includes taxes & fees
Dec 6 - Dec 7
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool area with chairs and a sign that reads 'POOLSIDE IS MY VIBE'.

8. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (799 reviews)
  • cleanliness
    Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.
The price is P9,624
P11,590 total
includes taxes & fees
Nov 19 - Nov 20
Home2 Suites by Hilton Middletown
An indoor swimming pool with a stone wall, lounge chairs, and a clear view of the outdoors.

9. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,256 reviews)
  • cleanliness
    Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
The price is P6,455
P7,624 total
includes taxes & fees
Dec 10 - Dec 11
Sleep Inn & Suites Middletown - Goshen
A pool area with lounge chairs and a hot tub.

10. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,011 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
The price is P6,442
P7,609 total
includes taxes & fees
Dec 13 - Dec 14
Courtyard by Marriott Middletown Goshen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub

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. 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 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 like 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.