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

Find Hotels with a Pool in Chester, NY

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chester hotels with a pool

An indoor water park with a large water slide, a pool area, and a glass ceiling structure.
A hotel with a pool area, outdoor seating, and a view of the sunset.
A modern building with a sign reading "The Kartrite Resort & Indoor Waterpark".
A modern apartment complex with a pool, outdoor seating, and a view of the sunset.

1. The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
Monticello
  • Splash into four-season aquatic fun at this family paradise with both indoor and outdoor pool playgrounds.
$270 nightly
$296 total
Oct 12 - Oct 13
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark
An indoor swimming pool with a 9-foot depth warning.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.

2. 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.
$118 nightly
$145 total
Nov 3 - Nov 4
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
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 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.

3. 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.
$220 nightly
$259 total
Oct 12 - Oct 13
Total with taxes and fees
LEGOLAND Hotel NEW York
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.

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.
$129 nightly
$159 total
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
An indoor swimming pool with lounge chairs and a stone wall.
A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

5. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
$102 nightly
$120 total
Nov 1 - Nov 2
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
A swimming pool with lounge chairs and umbrellas, surrounded by a fence, with a castle-like building in the background.
A spacious lobby with a staircase, seating area, and large windows offering a view of the outdoors.
A large, historic building with a red roof, surrounded by a well-maintained garden with statues and flower beds.
A historic stone building with a turret, arched entrance, and a covered patio area.

6. Tarrytown House Estate

Tarrytown House Estate
Tarrytown
  • Soak up sunshine or swim indoors at this peaceful Hudson River estate with seasonal pool options.
$191 nightly
$218 total
Nov 1 - Nov 2
Total with taxes and fees
Tarrytown House Estate
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 lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

7. 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.
$113 nightly
$134 total
Nov 3 - Nov 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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.
A lobby with a fireplace, seating area, and a reception desk.
A hotel room with a large bed, a sofa, a desk, and a bathroom.

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.
$118 nightly
$145 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn Harriman Woodbury
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.
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.
A large, two-story white house with a wrap-around porch and a small front garden.

9. 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.
$215 nightly
$243 total
Oct 8 - Oct 9
Total with taxes and fees
The Dominion House Bed & Breakfast
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 bar area with a curved counter, bar stools, and a television screen.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

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.
$101 nightly
$119 total
Oct 28 - Oct 29
Total with taxes and fees
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

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"The staff was helpful. Breakfast staff were amazing. Sunday rush was a lot! But they handled it very well and were so sweet"
Jacob 5-night trip
Posted less than an hour ago
Sleep Inn & Suites Middletown - Goshen
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 4 hours ago
Ramada by Wyndham Newburgh/West Point
Hampton Inn & Suites Mahwah

Hampton Inn & Suites Mahwah

10/10 Excellent
"I enjoyed my stay will stay again."
Isai 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Mahwah
Inn on the Hudson

Inn on the Hudson

8/10 Good
"Cute little inn! Rooms were clean however they need a little TLC. My friend complained of hearing the train horns during the night, but I slept right through it! The coffee machine in the lobby—the only coffee machine—was out of order."
Tracy 1-night trip
Posted 10 hours ago
Inn on the Hudson
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"The hotel was great. The only problem was there is an internal bar that was supposed to close at 11:00 pm but there was a lot of noise from the bar until after midnight."
Douglas 2-night trip
Posted 3 days ago
Crowne Plaza Suffern - Mahwah by IHG

Frequently asked questions

How much does a hotel with outdoor pool in Chester cost?
Enjoy staying in a hotel in Chester with an outdoor pool. You can find a great deal from $109 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels with outdoor pools that are close to LEGOLAND® New York?
The Holiday Inn Express Hotel & Suites Chester by IHG is an excellent choice for families seeking comfort and convenience near LEGOLAND® New York. With a traveller rating of 8.6, this hotel is well-loved for its friendly staff and clean, comfortable rooms, making it a great base for your adventures.Families will appreciate the outdoor pool, which offers a refreshing escape after a day of fun at the theme park. Guests have noted the pool area is well-maintained, superb for relaxing with sun loungers nearby. The hotel also provides a complimentary breakfast, including delicious options on weekends and even to-go breakfast bags, ensuring that busy mornings start off right.Moreover, with free self-parking and reliable Wi-Fi, this hotel combines quality and convenience, making your stay enjoyable without the hassle.
Are there hotels in Chester with outdoor pool activities or events?
Chester, New York, offers a charming retreat for travellers looking to enjoy a mix of natural beauty and upscale amenities. One standout option is the exquisite Glenmere Mansion, a luxury boutique hotel renowned for its stunning grounds and exceptional service. Here, guests can unwind in the heated outdoor swimming pool while taking in the picturesque surroundings. The property also features tennis, bocce, and croquet courts, ensuring plenty of recreational opportunities.For couples seeking a romantic getaway, Glenmere Mansion is an ideal choice. The opulent spa and bathhouse invite relaxation, while the beautifully landscaped gardens set the stage for intimate strolls. Special events, including wedding weekends held in the newly designed events barn, add a touch of magic to your stay, making it a great venue for celebrating love and commitment.Families will also find Chester appealing, as several hotels in the area boast outdoor pools, although specific activities may vary. These accommodations can serve as a convenient base for exploring nearby attractions like the serene Lake Glenmere or the beautiful hiking trails of the Hudson Valley.In summary, whether you're a couple looking to escape for a romantic weekend or a family eager for fun and relaxation, Chester provides delightful hotel options that cater to your needs.
Is it cheaper to book flights and a Chester hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Chester for you.

Explore a world of travel with Expedia