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Hotels with Swimming Pools in Chester

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Check availability on Chester Hotels with Swimming Pools

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 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 modern hotel lobby with a large map mural, seating areas, and a reception desk.
A Simon Premium Outlet sign at Woodbury Commons.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

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.
S$181
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 traditional living room with a chandelier, vintage furniture, and a fireplace.
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.

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.
S$311
includes taxes & fees
20 Oct - 21 Oct
The Dominion House Bed & Breakfast
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
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.
S$203
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
A restaurant with multiple dining tables and chairs, a central counter with a chef figure, and colorful hanging lights.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.

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.
S$360
includes taxes & fees
25 Oct - 26 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 lobby with a sofa, table, chairs, and a large window offering a view of greenery.
An outdoor patio with brick flooring, round tables, and blue umbrellas.
A hotel room with a large bed, a sofa, a desk, and a bathroom.

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.
S$186
includes taxes & fees
9 Nov - 10 Nov
Hampton Inn Harriman Woodbury
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

6. 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.
S$172
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 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.
A landscaped outdoor area with a fire feature, seating, and a pathway.

7. 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.
S$153
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Middletown Goshen
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 with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
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.

8. 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.
S$171
includes taxes & fees
2 Nov - 3 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool with lounge chairs and a stone wall.
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.
A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

9. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
S$153
includes taxes & fees
1 Nov - 2 Nov
Sleep Inn & Suites Middletown - Goshen
A swimming pool with four lounge chairs and a metal ladder.
A modern living room with a large TV, comfortable seating, and a patterned rug.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

10. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
S$179
includes taxes & fees
25 Oct - 26 Oct
Candlewood Suites Middletown Goshen by IHG
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"The property was nice as was the staff. However, the pool was also used for local swim lessons and the local swim team. Didn't mind that. But the hotel staff failed to tell us that and we were limited for the time to be in the pool. Or deal with 20-25 energetic kids. They also left all kinds of pool toys lying around the pool. Just some up front info would have been helpful."
MICHAEL 1-night trip
Posted 20 hours ago
Sleep Inn & Suites Middletown - Goshen
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Beautiful room nice and comfortable! Beautiful view out from the window"
James 3-night trip
Posted 1 day ago
Inn on the Hudson
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Hotel was in a good location."
WARREN 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chester by IHG
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"A+"
Kanwarpreet 2-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain

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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