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Find Hotels with a Pool in Chester, NY

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Our top choices for Chester hotels with a pool

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,024 reviews)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
$102 nightly
The price is $125
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,003 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
$110 nightly
The price is $130
Jul 15 - Jul 16
Total with taxes and fees
Courtyard by Marriott Middletown Goshen

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,008 reviews)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
$140 nightly
The price is $173
Jul 15 - Jul 16
Total with taxes and fees
Overlook Lodge at Bear Mountain

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.4 out of 10, Very Good, (1,009 reviews)
  • cleanliness
    Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
$105 nightly
The price is $124
Aug 10 - Aug 11
Total with taxes and fees
Hampton Inn by Hilton Middletown

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (235 reviews)
  • cleanliness
    Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
$215 nightly
The price is $243
Jul 13 - Jul 14
Total with taxes and fees
The Dominion House Bed & Breakfast

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1,130 reviews)
  • cleanliness
    Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.
$130 nightly
The price is $161
Jul 26 - Jul 27
Total with taxes and fees
Hampton Inn Harriman Woodbury

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,009 reviews)
  • cleanliness
    Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.
$109 nightly
The price is $129
Jul 12 - Jul 13
Total with taxes and fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
2.5 star property
Middletown
8.8 out of 10, Excellent, (737 reviews)
  • cleanliness
    Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.
$114 nightly
The price is $134
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (1,010 reviews)
  • cleanliness
    Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.
$124 nightly
The price is $147
Jul 26 - Jul 27
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.8 out of 10, Excellent, (1,074 reviews)
  • cleanliness
    Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
$110 nightly
The price is $130
Aug 2 - Aug 3
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

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 $124 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.
How can I save on a Chester hotel with a pool 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 our lowest Member Prices as well as members-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
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.

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