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Find Hotels with a Pool in Chester, NY

Check availability on Chester Hotels with a Pool

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

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 room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
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.
$122 nightly
$150 total
Aug 30 - Aug 31
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
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 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.

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.
$215 nightly
$243 total
Sep 7 - Sep 8
Total with taxes and fees
The Dominion House Bed & Breakfast
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 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.

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.
$129 nightly
$159 total
Sep 14 - Sep 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
A modern hotel lobby with a fireplace, comfortable seating, and a television.
A landscaped outdoor area with a fire feature, seating, and a pathway.
A modern hotel lobby with a seating area, large windows, and a television screen.

4. 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
Aug 30 - Aug 31
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
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.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

5. 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.
$97 nightly
$115 total
Sep 9 - Sep 10
Total with taxes and fees
Hampton Inn by Hilton Middletown
A swimming pool surrounded by a snow-covered landscape with a fence, a red umbrella, and a building in the background.
A kitchen with wooden cabinets, a black microwave, a black refrigerator, a stove, and a dishwasher.
A laundry facility with four washing machines, each with a digital display and control panel.
A hotel room with a large bed, a sofa, a coffee table, a fireplace, a TV, and a window with curtains.

6. Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #432

Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #432
Vernon
$330 nightly
$372 total
Aug 23 - Aug 24
Total with taxes and fees
Heated Pool Hot Tubs Sauna Gym Mtn Front Appalachian @ Mtn Creek #432

7. Ski-In/Ski-Out Mountain Creek 2BR | Renovated | Pool, Hot Tub, Fireplace

Ski-In/Ski-Out Mountain Creek 2BR | Renovated | Pool, Hot Tub, Fireplace
Vernon Township
$536 nightly
$536 total
Aug 27 - Aug 28
Total with taxes and fees
Ski-In/Ski-Out Mountain Creek 2BR | Renovated | Pool, Hot Tub, Fireplace

8. Large condo near Mountain Creek & Crystal Springs

Large condo near Mountain Creek & Crystal Springs
Vernon Township
$457 nightly
$516 total
Aug 31 - Sep 1
Total with taxes and fees
Large condo near Mountain Creek & Crystal Springs
An indoor swimming pool with lounge chairs and a stone wall.
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.
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.

9. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
$106 nightly
$126 total
Sep 10 - Sep 11
Total with taxes and fees
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 colorful play area with a check-in counter and a mascot.

10. 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.
$313 nightly
$369 total
Sep 7 - Sep 8
Total with taxes and fees
LEGOLAND Hotel NEW York
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
"Free breakfast was so good."
Ikuko 1-night trip
Posted less than an hour ago
Inn on the Hudson
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Room was clean."
Nicolas 1-night trip
Posted 15 hours ago
DoubleTree by Hilton Hotel Nanuet
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"This was a great place to stay."
randall 4-night trip
Posted 16 hours ago
Overlook Lodge at Bear Mountain
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent
"nice place"
Victor 1-night trip
Posted 1 day ago
Crowne Plaza Suffern - Mahwah by IHG
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

8/10 Good
"Very skeptical of staying at a Red Roof Inn as I think they have a bad rep, but we were very pleased with this hotel. It was very reasonable, the view was lovely of the river and the rooms were comfortable. Location wasn't great, especially if you don't have a vehicle (which we didn't) but if we had a car it would have been fine. Lots of parking."
Pamela 1-night trip
Posted 1 day ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Courtyard by Marriott Montvale

Courtyard by Marriott Montvale

10/10 Excellent
"Great location! Would stay there again"
Omar 1-night trip
Posted 1 day ago
Courtyard by Marriott Montvale
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Nice place to stay."
Antonio 1-night trip
Posted 4 days ago
Ramada by Wyndham Newburgh/West Point

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 $115 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.

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