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Hotels with Swimming Pool in Chester, New York

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Check availability on Chester Hotels with Swimming Pool

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 modern hotel lobby with a large map mural, seating areas, and a reception desk.
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.
P7,435
P9,154 total
includes taxes & fees
Sep 29 - Sep 30
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 dining table set outdoors with white chairs, a floral tablecloth, and a vase of flowers.
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.
P13,432
P15,195 total
includes taxes & fees
Oct 1 - Oct 2
The Dominion House Bed & Breakfast
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.

3. 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.
P8,378
P9,897 total
includes taxes & fees
Sep 29 - Sep 30
La Quinta Inn & Suites by Wyndham 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 circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.
A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.

4. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
P7,372
P8,708 total
includes taxes & fees
Oct 12 - Oct 13
Candlewood Suites Middletown Goshen by IHG
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
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.
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.

5. 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.
P7,435
P9,154 total
includes taxes & fees
Oct 26 - Oct 27
Fairfield Inn & Suites by Marriott Goshen Middletown
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 hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.
A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.

6. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
P6,877
P8,124 total
includes taxes & fees
Oct 19 - Oct 20
Sleep Inn & Suites Middletown - Goshen
A pool area with lounge chairs and a hot tub.
A modern hotel lobby with a fireplace, comfortable seating, and a television.
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.

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.
P6,585
P7,778 total
includes taxes & fees
Oct 12 - Oct 13
Courtyard by Marriott Middletown Goshen
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 room with a large bed, a sofa, a desk, and a bathroom.
A hotel lobby with a sofa, table, chairs, and a large window offering a view of greenery.

8. 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.
P7,633
P9,398 total
includes taxes & fees
Oct 5 - Oct 6
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 hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

9. 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.
P7,622
P9,003 total
includes taxes & fees
Oct 4 - Oct 5
Holiday Inn Express & 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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Was a pleasant overnight stay"
david 1-night trip
Posted 18 hours ago
Ramada by Wyndham Newburgh/West Point
Hilton Garden Inn Nanuet

Hilton Garden Inn Nanuet

8/10 Good
"Everything was fine in the room, but the beds were too cranky and a little uncomfortable."
Young mi 2-night trip
Posted 22 hours ago
Hilton Garden Inn Nanuet
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Everything was excellent. No complains"
Maria 1-night trip
Posted 22 hours ago
Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Beautiful and relaxing. Something I’d do different next time, I’d definitely stay at the Inn. As a solo female traveler, the Overlook was too secluded - it broke some of the solo traveling rules I’ve set for myself. Also, was a little bummed the next morning. Upon check in I was told about their Fall Foliage Buffet. I opted to do this instead of brunch the next day. Turns out that morning was a Princess Brunch, which canceled out the buffet and I had shown up after brunch hours. But the cafe was open and I was able to get a little something there."
Lindsay 1-night trip
Posted 1 day ago
Overlook Lodge at Bear Mountain
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Clean room, nice staff. Nice breakfast area added since I was last there. Very close to Paramount Theater and train station. Room had great view of the Hudson. Overall, a good overnight stay."
Laura 1-night trip
Posted 1 day ago
Inn on the Hudson
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

8/10 Good
"Nice hotel, needs a little updating."
Geraldine 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Nanuet

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. 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 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: Hotel, 1-minute walk from Mountain Creek Ski Resort. Offers 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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