A lake surrounded by autumn-colored trees reflecting on the water.

Find Hotels with a Pool in Middletown, NY

Check availability on Middletown Hotels with a Pool

Tonight
Oct 7 - Oct 8
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Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Middletown hotels with a pool

An indoor water park with a large water slide, a pool area, and a glass ceiling structure.
A hotel with a pool area, outdoor seating, and a view of the sunset.
A bar area with a central island, multiple bar stools, and a large screen displaying content.
A modern apartment complex with a pool, outdoor seating, and a view of the sunset.

1. The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
Monticello
  • Splash into four-season aquatic fun at this family paradise with both indoor and outdoor pool playgrounds.
$270 nightly
$296 total
Oct 12 - Oct 13
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark
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.

2. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
$102 nightly
$120 total
Nov 1 - Nov 2
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
An indoor swimming pool with clear water, surrounded by walls with a blue and white color scheme, and equipped with safety railings and seating areas.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

3. 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.
$113 nightly
$134 total
Nov 3 - Nov 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
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.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

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
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.
A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.
An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.
A spacious lobby with modern seating, a stone accent wall, and large windows offering views.

5. Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
  • Take a dip in the modern indoor pool at this Goshen hotel, offering year-round swimming in a spotlessly clean aquatic retreat.
$188 nightly
$222 total
Nov 1 - Nov 2
Total with taxes and fees
Residence Inn by Marriott Middletown Goshen
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 modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

6. 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.
$118 nightly
$139 total
Nov 5 - Nov 6
Total with taxes and fees
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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

7. 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.
$93 nightly
$109 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn by Hilton Middletown
An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.

8. 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.
$161 nightly
$193 total
Oct 26 - Oct 27
Total with taxes and fees
Home2 Suites by Hilton Middletown
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.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.

9. 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
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Goshen Middletown
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 colorful play area with a check-in counter and a mascot.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.

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.
$210 nightly
$247 total
Oct 12 - Oct 13
Total with taxes and fees
LEGOLAND Hotel NEW York
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Choose what matters most at hotels with a pool in Middletown

Breakfast included
Hot tub
Spa
4 stars
5 stars

Hotels with pools and free breakfast in Middletown

A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
$118 nightly
$139 total
Nov 5 - Nov 6
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A gym with treadmills, a weight bench, and various exercise equipment.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A hotel room with two beds, a desk, a TV, and a chair.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
$113 nightly
$134 total
Nov 3 - Nov 4
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A gym with exercise equipment, treadmills, and weight machines.

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
$93 nightly
$109 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn by Hilton Middletown
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A modern restaurant with a central island, multiple tables, and chairs.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
$161 nightly
$193 total
Oct 26 - Oct 27
Total with taxes and fees
Home2 Suites by Hilton Middletown
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
A modern lobby with a brown sofa, yellow armchairs, a patterned carpet, and a decorative plant centerpiece.
An indoor swimming pool with lounge chairs and a stone wall.
A hotel room with a bed, a flat-screen TV, a mini-fridge, a microwave, and a fireplace.

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
$102 nightly
$120 total
Nov 1 - Nov 2
Total with taxes and fees
Sleep Inn & Suites Middletown - Goshen
An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.
An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.
A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.
A spacious lobby with modern seating, a stone accent wall, and large windows offering views.

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
$188 nightly
$222 total
Nov 1 - Nov 2
Total with 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.
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Top Middletown Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"X"
Nicole 1-night trip
Posted 6 hours ago
Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"The complex was exactly that - complex. Initially, we drove to the Overlook Lodge to check in for our cabin only to find we needed to drive back down the mountain to the Inn (where ironically we had just been to turn around after missing the turn for Overlook Lodge!). The cabin was clean and quiet. The walk to and from the cabin to the Inn for dinner/morning coffee was lovely (along the lake)."
Thomas 1-night trip
Posted 7 hours ago
Overlook Lodge at Bear Mountain
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

8/10 Good
"Good value for the money. Convenient location. Nice room. Only issue was shower - it's a newish walkin which is great, but looks like it's been used hard."
Kim 1-night trip
Posted 9 hours ago
Courtyard by Marriott Middletown Goshen
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Very accommodating staff, they were able to move me to a room that didn't require stairs because I had a rolling cart with gear I needed to bring inside each night. I had to add a night to my reservation, so I bought another night there on Hotels.com, and they simply kept me in my same room so I didn't need to move anything. It was great! Good coffee available in the morning, easy location to get in and out of. They were actively renovating the property while I was there, so I don't count that towards the cleanliness of the property; everything was very clean, even while under renovation. Will stay again when needed!"
Brian 1-night trip
Posted 2 days ago
Ramada by Wyndham Newburgh/West Point
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

8/10 Good
"Good stay - was in town for a wedding- there were myths weekend. Staff was helpful."
Catherine 2-night trip
Posted 2 days ago
Hampton Inn by Hilton Middletown
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

10/10 Excellent
"We very much enjoyed our stay at this location. The staff was efficient and professional, our room was very clean and fresh smelling, the bed was comfortable and our room was quiet. The breakfast options were great and the host kept everything refilled as necessary. It's also in a good location. We would definitely stay there again."
Stan 1-night trip
Posted 2 days ago
Best Western Hunt's Landing Hotel Matamoras/Milford

Frequently asked questions

What are the best hotels in Middletown with outdoor pools?
For travellers seeking a refreshing retreat, the Holiday Inn Express & Suites Middletown - Goshen by IHG stands out with its inviting outdoor pool, rated an impressive 8.8 by guests. Families will appreciate the well-maintained pool area, superb for relaxation and fun after a day of exploration. The hotel also offers a complimentary breakfast that guests rave about, along with free toiletries and WiFi, making it a convenient choice for those traveling with children.Another excellent option is the Hampton Inn by Hilton Middletown, which boasts a cozy outdoor pool and receives high praise with a traveller rating of 8.6. Guests frequently mention the friendly staff and the spacious, clean rooms. The hotel's complimentary breakfast is known for its freshness, and the location strikes a balance between convenience and tranquility, ensuring a pleasant stay for families and adventure-seekers alike.Both of these hotels provide a blend of comfort and quality, making them ideal for families wanting to enjoy the outdoors while still having access to essential amenities.
How much does a hotel with outdoor pool in Middletown cost?
Enjoy staying in a hotel in Middletown with an outdoor pool. You can find a great deal from $90 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.
Is it cheaper to book flights and a Middletown 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 Middletown for you.

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