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Chester Hotels with Swimming Pool

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Check availability on Chester Hotels with Swimming Pools

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

Our top choices for Chester hotels with a pool

Indoor pool, pool loungers

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,020 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
The price is RM497
RM612 total
includes taxes & fees
26 Jul - 27 Jul
Holiday Inn Express Hotel & Suites Chester by IHG
Outdoor pool, pool loungers

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
  • cleanliness
    Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
The price is RM875
RM990 total
includes taxes & fees
13 Jul - 14 Jul
The Dominion House Bed & Breakfast
Seasonal outdoor pool

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very good, (1,007 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
The price is RM688
RM847 total
includes taxes & fees
12 Jul - 13 Jul
Overlook Lodge at Bear Mountain
Indoor pool

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very good, (1,008 reviews)
  • cleanliness
    Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.
The price is RM399
RM472 total
includes taxes & fees
26 Jul - 27 Jul
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
BBQ/picnic Area

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
The price is RM430
RM508 total
includes taxes & fees
3 Aug - 4 Aug
Hampton Inn by Hilton Middletown
Seasonal outdoor pool

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (630 reviews)
  • cleanliness
    Take a dip in the seasonal outdoor pool, a refreshing retreat with mountain views.
The price is RM469
RM530 total
includes taxes & fees
23 Jul - 24 Jul
Days Inn by Wyndham Wurtsboro
Outdoor spa tub

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 RM502
RM593 total
includes taxes & fees
26 Jul - 27 Jul
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Indoor pool

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,071 reviews)
  • cleanliness
    Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
The price is RM499
RM589 total
includes taxes & fees
2 Aug - 3 Aug
Sleep Inn & Suites Middletown - Goshen
Indoor pool

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
The price is RM446
RM527 total
includes taxes & fees
3 Aug - 4 Aug
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

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"The staff is very helpful and accommodating. The room was clean and comforting"
Elena 4-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Nanuet

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. Spark by Hilton Fishkill: Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Sleep Inn & Suites Middletown - Goshen: Offers a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet: Offers daily, an indoor pool and free self parking.
What is there to see and do in Chester?
Explore places such as LEGOLAND® New York and 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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