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Hotels with Swimming Pools in Chester

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Check availability on Chester Hotels with Swimming Pools

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, (1,024 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
The price is S$162
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 S$314
includes taxes & fees
13 Jul - 14 Jul
The Dominion House Bed & Breakfast
Indoor pool

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very good, (1,003 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
The price is S$167
includes taxes & fees
26 Jul - 27 Jul
Courtyard by Marriott Middletown Goshen
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, (1,008 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
The price is S$223
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, (1,009 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 S$150
includes taxes & fees
2 Aug - 3 Aug
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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 S$168
includes taxes & fees
23 Jul - 24 Jul
Days Inn by Wyndham Wurtsboro
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, (1,009 reviews)
  • cleanliness
    Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
The price is S$160
includes taxes & fees
5 Aug - 6 Aug
Hampton Inn 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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Room was clean when we arrived. Cleaning staff never can to pick up trash or towels or replace towels during our stay."
chasity 2-night trip
Posted less than an hour ago
Sleep Inn & Suites Middletown - Goshen

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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