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Find Hotels with a Pool in Chester, NY from CA $165

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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 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.
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.
CA $151
CA $185 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 garden with a stone fountain, a wooden gazebo, and various shrubs and flowers.
A traditional living room with a chandelier, vintage furniture, and a fireplace.
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.
CA $297
CA $336 total
includes taxes & fees
Sep 14 - Sep 15
The Dominion House Bed & Breakfast
A swimming pool with clear blue water, surrounded by trees and white fencing.
A spacious hallway with a wooden floor, a golden chair, and a staircase with white railings.
A hot tub with a wooden deck and railing, surrounded by a grassy area and a stone wall.
A large stone house with a dark roof, surrounded by lush green trees and a well-maintained lawn.

3. 11BR Retreat w Pool, Hot Tub, Sauna & Game Room

11BR Retreat w Pool, Hot Tub, Sauna & Game Room
Chester
CA $3,417
CA $5,353 total
includes taxes & fees
Sep 27 - Sep 28
11BR Retreat w Pool, Hot Tub, Sauna & Game Room
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 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 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.
CA $178
CA $219 total
includes taxes & fees
Oct 7 - Oct 8
Fairfield Inn & Suites by Marriott Goshen Middletown
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 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.

5. 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.
CA $163
CA $193 total
includes taxes & fees
Oct 6 - Oct 7
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 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.

6. 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.
CA $157
CA $194 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 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.
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

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.
CA $183
CA $217 total
includes taxes & fees
Sep 22 - Sep 23
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 hotel lobby with a fireplace, comfortable seating, and a television.
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.

8. 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.
CA $140
CA $165 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott 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 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.
CA $154
CA $182 total
includes taxes & fees
Oct 7 - Oct 8
Sleep Inn & Suites Middletown - Goshen
A swimming pool with four lounge chairs and a metal ladder.
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.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.

10. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
CA $148
CA $175 total
includes taxes & fees
Oct 6 - Oct 7
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

Courtyard by Marriott Mahwah

Courtyard by Marriott Mahwah

10/10 Excellent
"Very good."
Ibrahim 1-night trip
Posted 11 hours ago
Courtyard by Marriott Mahwah
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

8/10 Good
"On the first morning we couldn't get into the breakfast area, so we had to go out to diner and pay. when you are sold out you can get a seat to eat. This has happened other times during me stay at your properties."
richard 2-night trip
Posted 17 hours ago
Fairfield Inn & Suites by Marriott Goshen Middletown
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 1 day ago
Mountain Creek
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"Muy lindo hotel, limpio y con gran desayuno. El hall es impresionante y los jardines muy lindos. El gym chico pero sirve. Le falta a la zona un poco mas de opciones de comida. Pero vale la pena."
Jose roman 2-night trip
Posted 5 days ago
Crowne Plaza Suffern - Mahwah by IHG

Frequently asked questions

What are the best hotels in Chester with outdoor pools?
The Dominion House Bed & Breakfast is a charming option in Chester that offers an inviting outdoor pool, perfectly suited for families looking to unwind after a day filled with adventure. Rated an impressive 9.6 by travellers, guests rave about the warm atmosphere and thoughtful amenities, including free breakfast and toiletries, which add to the convenience of your stay.Another great choice is the Holiday Inn Express Hotel & Suites Chester by IHG, known for its clean and comfortable accommodations. This hotel boasts a well-kept outdoor pool complemented by sun loungers, making it a fantastic spot for families to relax. With a traveller review score of 8.4, guests frequently highlight the friendly staff and delicious breakfast options, ensuring a pleasant start to each day. Additionally, the hotel provides free Wi-Fi and convenient self-parking, further enhancing its appeal for families seeking both quality and value.
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 CA $165 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 looking for a convenient stay near LEGOLAND® New York. This 3-star hotel features a refreshing outdoor pool, superb for unwinding after a day of adventure. Guests appreciate the cleanliness of the pool area, making it a great spot for both kids and adults to relax.In addition to the pool, the hotel offers complimentary breakfast options, including delicious weekend spreads and convenient to-go choices, ensuring your family starts the day off right. With free WiFi and self-parking available, you'll find everything you need for a straightforward stay. Reviewers consistently highlight the friendly and helpful staff, as well as the comfortable and clean rooms, contributing to a friendly setting.
Are there hotels in Chester with outdoor pool activities or events?
Chester, New York, is a picturesque destination that offers a delightful escape into nature, making it superb for those seeking relaxation and adventure. For travellers looking for hotels with outdoor pool activities, the luxurious Glenmere Mansion is a great choice. This boutique hotel features a heated outdoor swimming pool, allowing guests to unwind while enjoying the scenic beauty of the surrounding landscape. In addition to the pool, Glenmere Mansion boasts tennis, bocce, and croquet courts, providing ample opportunities for active leisure right on the property.For couples wanting a romantic getaway, Glenmere Mansion offers an elegant stay complemented by a world-acclaimed spa and bath house. Imagine indulging in soothing treatments before enjoying a refreshing dip in the pool, or perhaps unwinding with a glass of wine on the terrace as the sun sets.Families will also find Chester appealing, with various outdoor activities to engage the kids. While Glenmere Mansion caters to a luxury experience, nearby accommodations may offer more casual settings with outdoor pools, superb for families looking to splash around together.
Is it cheaper to book flights and a hotel in Chester 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 travel 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 with an outdoor pool in Chester for you.
How can I save on a hotel in Chester with Expedia?
Before booking your Chester hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

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