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Find Hotels with a Pool in Chester, NY from CA $132

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Check availability on Chester Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 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.
CA $150
CA $184 total
includes taxes & fees
Nov 22 - Nov 23
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 dining table set outdoors with white chairs, a floral tablecloth, and a vase of 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.
CA $151
CA $170 total
includes taxes & fees
Nov 9 - Nov 10
The Dominion House Bed & Breakfast
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 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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.

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.
CA $181
CA $222 total
includes taxes & fees
Nov 3 - Nov 4
Fairfield Inn & Suites by Marriott Goshen Middletown
A swimming pool with colorful umbrellas and lounge chairs.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
A LEGO display with a large red sign reading 'BRICKS RECIPE BOOK' by S. Platt, featuring LEGO figures and a colorful LEGO building.
A colorful play area with a check-in counter and a mascot.

4. 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.
CA $178
CA $394 total
includes taxes & fees
Nov 1 - Nov 2
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 hotel with a modern facade, multiple floors, and a covered entrance area.
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 $171
CA $202 total
includes taxes & fees
Nov 8 - Nov 9
Holiday Inn Express & Suites Middletown - Goshen by IHG
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A gym with exercise equipment, treadmills, and weight machines.

6. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
  • Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
CA $112
CA $132 total
includes taxes & fees
Nov 19 - Nov 20
Hampton Inn by Hilton Middletown
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 modern bar area with a curved counter, bar stools, 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.
CA $142
CA $167 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Middletown Goshen
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 hotel entrance with a covered walkway, a prominent sun logo, and a modern facade.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

8. 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 $149
CA $176 total
includes taxes & fees
Nov 18 - Nov 19
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 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.
CA $142
CA $167 total
includes taxes & fees
Nov 19 - Nov 20
Sleep Inn & Suites Middletown - Goshen
An indoor swimming pool area with chairs and a sign that reads 'POOLSIDE IS MY VIBE'.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
An outdoor patio with a barbecue grill, seating area, and potted plants.
A hotel room with a kitchenette, including a microwave, coffee maker, and sink.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
  • Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.
CA $157
CA $190 total
includes taxes & fees
Nov 4 - Nov 5
Home2 Suites by Hilton Middletown
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

Inn on the Hudson

Inn on the Hudson

8/10 Good
"staff fixed number of beds we wanted. No exercise area, though there a big room they could use."
carol 4-night trip
Posted less than an hour ago
Inn on the Hudson
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

8/10 Good
"They have begun to charge $10 to park on the property which is kind of ridiculous , not to many happy guests with the new policy."
greg 1-night trip
Posted 3 days ago
Crowne Plaza Suffern - Mahwah by IHG
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Was under construction, room was clean and comfortable."
Gary 4-night trip
Posted 4 days ago
Ramada by Wyndham Newburgh/West Point

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 $132 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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