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Chester Hotel Guide - Hotels with Pool in Chester, New York

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Check availability on Chester Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chester hotels with a pool

An indoor swimming pool with a 9-foot depth warning.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.
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.

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.
€123
includes taxes & fees
10 Nov - 11 Nov
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.
€109
includes taxes & fees
9 Nov - 10 Nov
The Dominion House Bed & Breakfast
A deck with outdoor seating, a hot tub, and a swimming pool surrounded by greenery.
An aerial view of a large, two-story house surrounded by dense forest, with a swimming pool and outdoor seating area.
A wooden deck with outdoor furniture, a pool, and a lush garden.
A brick fireplace with a glass screen, a potted plant, and a shelf with decorative items.

3. Serene 10BR Retreat w/Pool, Gym & Hot Tub

Serene 10BR Retreat w/Pool, Gym & Hot Tub
Chester
€2,461
includes taxes & fees
18 Oct - 19 Oct
Serene 10BR Retreat w/Pool, Gym & Hot Tub
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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

4. 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.
€142
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Goshen Middletown
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 hotel room with two beds, a desk, a TV, and a chair.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

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.
€115
includes taxes & fees
10 Nov - 11 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool with lounge chairs and a stone wall.
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.
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.
€107
includes taxes & fees
8 Nov - 9 Nov
Sleep Inn & Suites Middletown - Goshen
A swimming pool with colorful umbrellas and lounge chairs.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.
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.

7. 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.
€251
includes taxes & fees
18 Oct - 19 Oct
LEGOLAND Hotel NEW York
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.

8. 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.
€121
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
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.
A lobby with a fireplace, seating area, and a reception desk.
An outdoor patio with brick flooring, round tables, and blue umbrellas.

9. 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.
€130
includes taxes & fees
26 Oct - 27 Oct
Hampton Inn Harriman Woodbury
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
A modern hotel lobby with a fireplace, comfortable seating, and a television.
A modern hotel lobby with a seating area, large windows, and a television screen.
A landscaped outdoor area with a fire feature, seating, and a pathway.

10. 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.
€107
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott 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

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"This is a quaint room in like a summer camp cabin. You can’t control your own heating and air conditioning - take note. The rooms were very clean and basic. I would stay again as the grounds are incredible and we had an awesome time outdoors."
Khai 2-night trip
Posted 1 hour ago
Overlook Lodge at Bear Mountain
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

8/10 Good
"IT WAS HARD FINDING A PARKING SPOT. I TFOUND THE PERSON AT THE FRONT DESK NOT VERY WELCOMING."
betty 1-night trip
Posted 9 hours ago
Hampton Inn & Suites Mahwah
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

8/10 Good
"Parking was great"
Kathie Campbell 3-night trip
Posted 13 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"Friendly staff clean property nice amenities"
Rashean 1-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Chester by IHG
Inn on the Hudson

Inn on the Hudson

10/10 Excellent
"Common balcony was nice but it was a surprise."
joyce 1-night trip
Posted 2 days ago
Inn on the Hudson

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.