Find Hotels with a Pool in Chester, NY

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Check prices for these dates

Tonight
10 Nov - 11 Nov
Tomorrow
11 Nov - 12 Nov
This weekend
13 Nov - 15 Nov
Next weekend
20 Nov - 22 Nov

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, (1,004 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
The price is AED 356
AED 439 total
includes taxes & fees
15 Nov - 16 Nov
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 AED 790
AED 893 total
includes taxes & fees
16 Nov - 17 Nov
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, (1,005 reviews)
  • cleanliness
    Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
The price is AED 474
AED 583 total
includes taxes & fees
11 Nov - 12 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.

4. 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 AED 327
AED 868 total
includes taxes & fees
13 Nov - 14 Nov
LEGOLAND Hotel NEW York
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 AED 353
AED 417 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express & Suites Middletown - Goshen by IHG
A pool area with a hot tub, a pool lift, and safety signs on the walls.

6. 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, (1,008 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 AED 415
AED 490 total
includes taxes & fees
6 Dec - 7 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool with clear blue water, surrounded by tiled flooring and furnished with chairs and tables.

7. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,157 reviews)
  • cleanliness
    Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
The price is AED 409
AED 504 total
includes taxes & fees
1 Dec - 2 Dec
Hampton Inn Harriman Woodbury
An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

8. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (353 reviews)
  • cleanliness
    Take a dip in the modern indoor pool at this Goshen hotel, offering year-round swimming in a spotlessly clean aquatic retreat.
The price is AED 657
AED 777 total
includes taxes & fees
29 Nov - 30 Nov
Residence Inn by Marriott Middletown Goshen
A pool area with lounge chairs and a hot tub.

9. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,010 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
The price is AED 387
AED 457 total
includes taxes & fees
19 Nov - 20 Nov
Courtyard by Marriott Middletown Goshen
An indoor swimming pool area with chairs and a sign that reads 'POOLSIDE IS MY VIBE'.

10. 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 AED 559
AED 673 total
includes taxes & fees
19 Nov - 20 Nov
Home2 Suites by Hilton Middletown
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

Top Chester Hotel Reviews

An indoor swimming pool with a 9-foot depth warning.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester

10/10 Excellent

The hotel is new so everything is fresh, clean and beautiful. My husband and I are retired seniors and loved the fact that it was only a shower. Often a tub does not have a rough surface on the bottom to prevent slipping. So the shower was just perfect. We were upgraded to a suite that was just gorgeous. Could not have been better.
United States
Jeris
Reviewed November 9, 2026
Holiday Inn Express Hotel & Suites Chester by IHG

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.