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Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Tonight
Sep 8 - Sep 9
Tomorrow
Sep 9 - Sep 10
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chester hotels with a pool

An indoor swimming pool with a 9-foot depth warning.
A Simon Premium Outlet sign at Woodbury Commons.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.

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.
NT$3,439
NT$4,234 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Express Hotel & Suites Chester by IHG
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.
A large, two-story white house with a wrap-around porch and a small front garden.
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.

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.
NT$6,783
NT$7,673 total
includes taxes & fees
Sep 14 - Sep 15
The Dominion House Bed & Breakfast
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee 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.
NT$4,070
NT$5,011 total
includes taxes & fees
Oct 7 - Oct 8
Fairfield Inn & Suites by Marriott Goshen Middletown
An indoor swimming pool with clear blue water, surrounded by tiled flooring and furnished with chairs and tables.
An outdoor patio with brick flooring, round tables, and blue umbrellas.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.
A lobby with a fireplace, seating area, and a reception desk.

4. 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.
NT$3,596
NT$4,428 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Inn Harriman Woodbury
A pool area with a hot tub, a pool lift, and safety signs on the walls.
A hotel room with two beds, a desk, a TV, and a chair.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A modern bathroom with a large mirror, a sink, and a shower.

5. 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.
NT$4,231
NT$4,998 total
includes taxes & fees
Sep 13 - Sep 14
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
A modern bar area with a curved counter, bar stools, and a television screen.
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.

6. 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.
NT$3,191
NT$3,770 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott Middletown Goshen
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
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.
NT$3,723
NT$4,398 total
includes taxes & fees
Oct 6 - Oct 7
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with four lounge chairs and a metal ladder.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.
A modern living room with a large TV, comfortable seating, and a patterned rug.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

8. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
NT$3,376
NT$3,988 total
includes taxes & fees
Oct 6 - Oct 7
Candlewood Suites Middletown Goshen by IHG
An indoor swimming pool with lounge chairs and a stone wall.
A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.
A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.
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.
NT$3,505
NT$4,140 total
includes taxes & fees
Oct 7 - Oct 8
Sleep Inn & Suites Middletown - Goshen
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

Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"An excellent location for the purpose of our visit - clean and quiet with a very helpful staff."
mary 2-night trip
Posted less than an hour ago
Crowne Plaza Suffern - Mahwah by IHG
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good
"Room was nice and clean no issues and ample space."
Rodolfo 1-night trip
Posted 5 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Excellent place, excellent staff and the restaurant has excellent food as well. Second stay in this hotel in the last 6 months and will definitely be staying there."
Hilda 2-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"The room was clean at the cottage. The common area was useful."
David 2-night trip
Posted 7 hours ago
Overlook Lodge at Bear Mountain
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

10/10 Excellent
"This Red Roof Inn is very clean and the staff is friendly. Minor complain is that the floors feels like there is a film on it that feels a bit slippery, probably from build up of cleaning agent, but room is clean. I enjoyed my stay."
Adrienne 1-night trip
Posted 10 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

10/10 Excellent
"Very good."
Ibrahim 1-night trip
Posted 1 day ago
Courtyard by Marriott Mahwah
Mountain Creek

Mountain Creek

8/10 Good
"I liked the room, I was surprised there was no door for our one bedroom suite. It was also shocking to me that no staff came during our 4 day stay to come remove the filled trash bin. It seemed like the resort was low on staff. But the pool was great to swim and relax in, and I was pleased they were open for long hours. Our room was cozy and the view was lovely."
Gabriella 3-night trip
Posted 2 days ago
Mountain Creek

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. Sleep Inn & Suites Middletown - Goshen: Offers continental, an indoor pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: 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 free self parking, an indoor pool, and complimentary wireless internet access. Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Hotel, 1-minute walk from Mountain Creek Ski Resort. Features a sauna, an outdoor pool, and a snack bar/deli.
What is there to see and do in Chester?
Explore places like Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like 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 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.

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