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Find Hotels with an Outdoor Pool in Middletown, NY

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Our top choices for Middletown hotels with an outdoor pool

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1007)
"Room was clean and staff was great!"
United States
Annemarie
$75 nightly
The price is $89
Jan 7 - Jan 8, 2026
Total with taxes and fees
Hampton Inn by Hilton Middletown

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1004)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
$102 nightly
The price is $116
Jan 12 - Jan 13, 2026
Total with taxes and fees
Overlook Lodge at Bear Mountain

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1003)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
$101 nightly
The price is $124
Dec 29 - Dec 30
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
$294 nightly
The price is $346
Jan 2 - Jan 3, 2026
Total with taxes and fees
LEGOLAND Hotel NEW York

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
4.0 star property
Monticello
8.2 out of 10, Very Good, (1874)
"Friendly staff , clean , beautiful design in the hotel and decor . "
United States
Lusvianca
$216 nightly
The price is $244
Jan 8 - Jan 9, 2026
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (596)
"Very clean and quiet "
United States
Jeanette
$95 nightly
The price is $107
Dec 28 - Dec 29
Total with taxes and fees
Days Inn by Wyndham Wurtsboro

Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection
5.0 star property
Gardiner
9.4 out of 10, Exceptional, (58)
"Everything was ok, except for the fact that we couldn’t do late check out or that we payed a bit more for a standard room. But everything else was perfect "
United States
Sandra N
$1,238 nightly
The price is $1,387
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wildflower Farms, Auberge Collection

Mountain Creek

Mountain Creek
3.0 star property
Vernon
8.2 out of 10, Very Good, (653)
"Glad i stay very nice hotel"
United States
David
$308 nightly
The price is $352
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mountain Creek

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
$215 nightly
The price is $243
Dec 29 - Dec 30
Total with taxes and fees
The Dominion House Bed & Breakfast

Harvest Inn

Harvest Inn
2.5 star property
Pine Bush
9.4 out of 10, Exceptional, (560)
"Breakfast was great, but the walls are paper thin like paper thin I got the couple that came in next-door didn’t get it on."
United States
Ken
$219 nightly
The price is $248
Jan 2 - Jan 3, 2026
Total with taxes and fees
Harvest Inn
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.

Find out more about Middletown

Discover top Middletown attractions

Middletown, New York, offers a delightful mix of relaxation and adventure, perfect for travelers seeking hotels with pools for a refreshing retreat. Start your day at the scenic Highland Lakes, where you can enjoy serene walks or a leisurely picnic by the water, surrounded by lush greenery. The nearby Orange County Arboretum is a peaceful haven, featuring beautifully landscaped gardens that are perfect for a tranquil stroll or a family outing. For a touch of history, visit the Paramount Theatre for a glimpse at local performances, or venture out to the nearby Museum Village, where you can explore interactive exhibits that bring the past to life. If you're in the mood for shopping, the Galleria at Crystal Run offers an array of stores and dining options, providing a relaxed atmosphere to unwind. For accommodations, consider the hotels located near the city center, where you can enjoy stunning views, on-site pools, and attentive service, ensuring that your stay is as rejuvenating as it is enjoyable. Whether you're lounging by the pool or exploring the local attractions, Middletown promises a memorable experience for the quality-seeking traveler.

Find the best hotels with an outdoor pool in Middletown

For travelers looking to enjoy refreshing dips during their stay in Middletown, New York, these hotels with outdoor pools provide the perfect escape. Relax and unwind under the sun with these top choices.

Holiday Inn Express & Suites Middletown - Goshen by IHG

  • Why it's great for poolside lounging: The Holiday Inn Express & Suites Middletown - Goshen is an ideal choice for travelers seeking an inviting outdoor pool experience, an excellent guest review rating of 8.6. Guests can soak up the sun on the pool sun loungers or enjoy the accessible pool, making it a great spot for relaxation and leisure.
  • Other amenities: This hotel also features an indoor pool for year-round swimming, free breakfast options daily, and convenient contactless check-in. Additional offerings include accessible parking, daily housekeeping, and a concierge service, ensuring a comfortable stay. Guests can explore nearby wineries and shopping centers, enhancing their experience in the charming Middletown area.
  • Nearby attractions: Galleria at Crystal Run - 1.52 miles, Orange County Fair Speedway - 1.39 miles

Hampton Inn by Hilton Middletown

  • Why it's great for poolside lounging: The Hampton Inn by Hilton Middletown offers a delightful stay for guests looking to enjoy an outdoor pool, featuring a solid review rating of 8.4. The accessible outdoor pool invites travelers to relax and unwind after a long day of exploring, making it a perfect retreat.
  • Other amenities: Guests at this hotel can enjoy complimentary breakfast options, a terrace for outdoor seating, and a fitness center to stay active during their stay. Additional features include free self-parking, daily housekeeping, and various nearby recreational activities like skiing and hiking. The friendly atmosphere and convenient amenities make this hotel a great choice for those seeking comfort and relaxation.
  • Nearby attractions: Galleria at Crystal Run - 1.42 miles, Highland Lakes State Park - 2.69 miles

Top Middletown Hotel Reviews

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