A green agricultural field with rows of crops and greenhouses in the distance under a cloudy sky.

Chester Hotels with Swimming Pool

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Check availability on Chester Hotels with Swimming Pools

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chester hotels with a pool

An indoor swimming pool with a 9-foot depth warning.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A Simon Premium Outlet sign at Woodbury Commons.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
  • Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
RM400
RM493 total
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express Hotel & Suites Chester by IHG
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.
A garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.
A large, two-story white house with a wrap-around porch and a small front garden.
A dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
Chester
  • Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
RM878
RM994 total
includes taxes & fees
12 Oct - 13 Oct
The Dominion House Bed & Breakfast
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

3. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen
  • Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
RM527
RM649 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.
A colorful play area with a check-in counter and a mascot.
A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.

4. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
  • Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.
RM442
RM1,057 total
includes taxes & fees
12 Oct - 13 Oct
LEGOLAND Hotel NEW York
An indoor swimming pool with clear blue water, surrounded by tiled flooring and furnished with chairs and tables.
A hotel room with a large bed, a sofa, a desk, and a bathroom.
An outdoor patio with brick flooring, round tables, and blue umbrellas.
A lobby with a fireplace, seating area, and a reception desk.

5. Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
Central Valley
  • Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
RM483
RM594 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Harriman Woodbury
An indoor swimming pool with clear water, surrounded by walls with a blue and white color scheme, and equipped with safety railings and seating areas.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A hotel room with two beds, a desk, a TV, and a chair.
A modern bathroom with a large mirror, a sink, and a shower.

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

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
  • Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.
RM462
RM546 total
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

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

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
  • Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.
RM466
RM550 total
includes taxes & fees
8 Nov - 9 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
A landscaped outdoor area with a fire feature, seating, and a pathway.
A modern hotel lobby with a seating area, large windows, and a television screen.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

8. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
  • Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
RM413
RM488 total
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Middletown Goshen
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.
A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.
A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.
A spacious lobby with modern seating, a stone accent wall, and large windows offering views.

9. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
  • Take a dip in the modern indoor pool at this Goshen hotel, offering year-round swimming in a spotlessly clean aquatic retreat.
RM768
RM907 total
includes taxes & fees
1 Nov - 2 Nov
Residence Inn by Marriott Middletown Goshen
An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A modern restaurant with a central island, multiple tables, and chairs.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
  • Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.
RM656
RM790 total
includes taxes & fees
26 Oct - 27 Oct
Home2 Suites by Hilton Middletown
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"😊"
Dorine 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Nanuet
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"This is my fourth visit to this location, and I plan to continue staying here in the future. The scenery is beautiful, the rooms are clean, the staff is wonderful, and everything is perfect."
debra a 2-night trip
Posted 1 day ago
Inn on the Hudson
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Very accommodating staff, they were able to move me to a room that didn't require stairs because I had a rolling cart with gear I needed to bring inside each night. I had to add a night to my reservation, so I bought another night there on Hotels.com, and they simply kept me in my same room so I didn't need to move anything. It was great! Good coffee available in the morning, easy location to get in and out of. They were actively renovating the property while I was there, so I don't count that towards the cleanliness of the property; everything was very clean, even while under renovation. Will stay again when needed!"
Brian 1-night trip
Posted 2 days ago
Ramada by Wyndham Newburgh/West Point

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. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool and complimentary high-speed (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 such as 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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