Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Chester Hotels with a Pool

Indoor pool, sun loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
  • Indoor pool
  • Pool loungers
8.6 out of 10, Excellent, (1009)
Splash into vacation mode at the pristine indoor pool, complete with inviting sun loungers for post-swim relaxation. Families appreciate the hotel's proximity to LEGOLAND New York while enjoying spotlessly clean rooms with premium bedding and thoughtful amenities.
The price is SAR 360
SAR 425 total
includes taxes & fees
3 Dec - 4 Dec
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

2.0 star property
Chester
  • Outdoor pool
9.2 out of 10, Wonderful, (233)
Swimming enthusiasts delight in the sparkling outdoor pool surrounded by scenic gardens at this charming bed and breakfast. After morning hikes on nearby trails, guests savor outstanding, filling breakfasts before relaxing poolside or enjoying the arcade room.
The price is SAR 807
SAR 912 total
includes taxes & fees
1 Dec - 2 Dec
The Dominion House Bed & Breakfast
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
  • Outdoor pool
8.6 out of 10, Excellent, (30)
Pool toys transform the outdoor pool into a delightful aquatic playground at this LEGOLAND hotel. After swimming, families can enjoy the on-site restaurant, arcade room, and garden, making this vibrant getaway perfect for creating lasting memories.
The price is SAR 579
SAR 1,139 total
includes taxes & fees
26 Dec - 27 Dec
LEGOLAND Hotel NEW York
Indoor pool
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

2.5 star property
Fishkill
  • Indoor pool
  • Hot tub
8.4 out of 10, Very Good, (1004)
Refreshing waters beckon in the immaculate indoor pool, complemented by a soothing hot tub that guests consistently praise. Beyond aquatic amenities, visitors enjoy comfortable rooms with premium bedding and a complimentary breakfast buffet each morning.
The price is SAR 330
SAR 373 total
includes taxes & fees
26 Dec - 27 Dec
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
  • Full-service spa
8.4 out of 10, Very Good, (1023)
Seasonal outdoor swimming invites summer splashes amid breathtaking mountain scenery. After hiking local trails, guests rejuvenate with spa treatments, including deep-tissue massages and facials, before enjoying fresh cuisine at the onsite café.
The price is SAR 379
SAR 429 total
includes taxes & fees
7 Dec - 8 Dec
Overlook Lodge at Bear Mountain
Indoor pool, open 8:30 AM to 9:30 PM, sun loungers
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4.0 star property
Nanuet
  • Indoor pool
  • Pool loungers
  • Hot tub
8.8 out of 10, Excellent, (1011)
Gliding through crystal-clear waters, swimmers enjoy this hotel's immaculate indoor pool before unwinding in the rejuvenating hot tub. Clean, comfortable rooms complement the fitness center and Windsor Grille restaurant, creating a peaceful retreat near Palisades Center.
The price is SAR 397
SAR 462 total
includes taxes & fees
14 Dec - 15 Dec
DoubleTree by Hilton Hotel Nanuet
BBQ/picnic area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 star property
Middletown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
8.6 out of 10, Excellent, (1005)
Dive into summer refreshment at the seasonal outdoor pool, open from May through September. Beyond swimming, this hotel entices with nearby adventures including hiking trails, kayaking, and mountain biking, plus a modern fitness center for year-round activity.
The price is SAR 294
SAR 347 total
includes taxes & fees
23 Dec - 24 Dec
Hampton Inn by Hilton Middletown
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
  • Indoor pool
8.6 out of 10, Excellent, (1009)
Swimmers enjoy year-round aquatic bliss at the temperature-controlled indoor pool, a perfect complement to the comprehensive 24-hour fitness center. Adventure seekers appreciate nearby hiking trails, while business travelers value the laptop-friendly workspaces.
The price is SAR 344
SAR 389 total
includes taxes & fees
8 Dec - 9 Dec
Hilton Garden Inn Fishkill
Indoor pool
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
Middletown
  • Indoor pool
9.4 out of 10, Exceptional, (923)
Sparkling waters await in the tranquil indoor pool area, open daily from 9:00 AM to 9:00 PM for refreshing swims regardless of weather. Guests praise the spotless facilities, including a rejuvenating hot tub and well-equipped fitness center for complete vacation balance.
The price is SAR 395
SAR 467 total
includes taxes & fees
17 Dec - 18 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Seasonal outdoor pool
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
Goshen
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (1003)
Swimming sessions in the seasonal outdoor pool create perfect summer memories at this exceptionally clean hotel. Complementing aquatic enjoyment, guests appreciate the 24-hour fitness center, complimentary breakfast buffet, and consistently helpful staff.
The price is SAR 348
SAR 428 total
includes taxes & fees
16 Dec - 17 Dec
Fairfield Inn & Suites by Marriott Goshen 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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Top Chester Hotel Reviews

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

10/10 Excellent
"Great customer service "
Dwight 2-night trip
Posted 2 days ago
Courtyard by Marriott Mahwah

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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. Sonesta Simply Suites Nanuet: Provides a snack bar/deli, a pool, and free self parking. DoubleTree by Hilton Hotel Nanuet: 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: Offers full, a pool, and complimentary wired internet access. Hampton Inn & Suites Mahwah: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access.
What is there to see and do in Chester?
Make a point to visit attractions like The Rock Sports Complex and Castle Fun Center. Discover sights such as Goosepond Mountain State Park and Museum Village during your stay. 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.