Photo by Vincent Ramundo

Find Hotels with a Pool in Middletown, NY

Check availability on Middletown Hotels with a Pool

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Tonight
Aug 2 - Aug 3
Tomorrow
Aug 3 - Aug 4
Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17

Top Middletown Hotels with a Pool

Hampton Inn Harriman Woodbury
Relax by the pool surrounded by lush greenery and enjoy a refreshing swim.

Hampton Inn Harriman Woodbury

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Great stay great staff great accommodations "
$127 nightly
The price is $156
Sep 1 - Sep 2
Total includes taxes and fees
Hampton Inn Harriman Woodbury
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Relax by the pool with easy access via the central ladder and comfortable seating areas.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
9.2 out of 10, Wonderful, (771)
"Place was great have stayed here many times."
$116 nightly
The price is $137
Aug 3 - Aug 4
Total includes taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Sleep Inn & Suites Middletown - Goshen
Relax by the pool surrounded by artwork and comfortable seating.

Sleep Inn & Suites Middletown - Goshen

2.5 star property
8.6 out of 10, Excellent, (1012)
"Staff was very kind and breakfast was good "
$97 nightly
The price is $114
Aug 24 - Aug 25
Total includes taxes and fees
Sleep Inn & Suites Middletown - Goshen
Fairfield Inn & Suites by Marriott Goshen Middletown
Relax by the pool surrounded by lounge chairs and umbrellas.

Fairfield Inn & Suites by Marriott Goshen Middletown

2.5 star property
8.8 out of 10, Excellent, (976)
"Great breakfast, great room. "
$110 nightly
The price is $135
Aug 24 - Aug 25
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
Holiday Inn Express Hotel & Suites Chester by IHG
Relax by the pool, surrounded by lounge chairs and a seating area with tables.

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
8.4 out of 10, Very Good, (1003)
"Very clean and breakfast was worthy."
$127 nightly
The price is $150
Aug 10 - Aug 11
Total includes taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
Courtyard by Marriott Middletown Goshen
Relax by the pool surrounded by comfortable lounge chairs and a clear water surface.

Courtyard by Marriott Middletown Goshen

3.0 star property
8.6 out of 10, Excellent, (937)
"The room was clean and beautiful and we loved the indoor pool highly recommend. "
$101 nightly
The price is $119
Aug 10 - Aug 11
Total includes taxes and fees
Courtyard by Marriott Middletown Goshen
Hampton Inn by Hilton Middletown
Relax by the pool surrounded by a shaded patio with a table and comfortable seating.

Hampton Inn by Hilton Middletown

2.5 star property
8.6 out of 10, Excellent, (1004)
"Stay was pleasant "
$103 nightly
The price is $122
Aug 24 - Aug 25
Total includes taxes and fees
Hampton Inn by Hilton Middletown
Holiday Inn Express & Suites Middletown - Goshen by IHG
Relax by the rectangular pool surrounded by a tiled deck and enjoy the convenience of a pool lift.

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 star property
8.8 out of 10, Excellent, (670)
"The rooms are welcoming and clean. Children loved the morning breakfast provided by the hotel. "
$145 nightly
The price is $171
Aug 3 - Aug 4
Total includes taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
Home2 Suites by Hilton Middletown
Relax by the pool surrounded by comfortable lounge chairs and a small table.

Home2 Suites by Hilton Middletown

3.0 star property
9.0 out of 10, Wonderful, (706)
"Been here twice and very family friendly "
$144 nightly
The price is $173
Aug 10 - Aug 11
Total includes taxes and fees
Home2 Suites by Hilton Middletown
Residence Inn by Marriott Middletown Goshen
Swim laps in the rectangular pool surrounded by a tiled deck and informative signs.

Residence Inn by Marriott Middletown Goshen

3.0 star property
9.4 out of 10, Exceptional, (304)
"Great place to stay!. "
$184 nightly
The price is $217
Aug 10 - Aug 11
Total includes taxes and fees
Residence Inn by Marriott 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.

Top Middletown Hotel Reviews

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Great price. Wonderful location. Will be back!"
Suzanne 1-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain

Frequently asked questions

What's it like visiting Middletown?
If laying by the pool is your idea of the perfect getaway, you may want to check out family-friendly Middletown, which offers 6 places to stay with pools. While you're visiting, you can explore sights such as Woodbury Common Premium Outlets and LEGOLAND® New York, and then relax poolside at one of the accommodations in Middletown that guests like for their pools.
What are some accommodations with pools in Middletown?
La Quinta Inn & Suites by Wyndham Middletown-Goshen: Features daily, an indoor pool, and free self parking. Sleep Inn & Suites Middletown - Goshen: Offers continental, an indoor pool, and complimentary wired internet access. Courtyard by Marriott Middletown Goshen: Provides complimentary wired internet access, an indoor pool, and free self parking. Hampton Inn by Hilton Middletown: Features daily, a seasonal outdoor pool, and complimentary wired internet access. Super 8 by Wyndham Middletown: Offers daily, an indoor pool, and complimentary wired internet access.
How many hotels with pools are there in Middletown?
Expedia has 6 hotels in Middletown for your poolside break.
What is there to see and do in Middletown?
Explore places like LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. The picturesque setting of Highland Lake and Thomas Bull Memorial Park showcase the area's natural beauty. Travelers love Middletown for its array of dining options.
When is the best time to book a hotel with a pool in Middletown?
Taking into account the local weather in Middletown can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Middletown are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.