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

Middletown Hotel Guide - Hotels with Pool in Middletown, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown Hotels with Pool

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

Our top choices for Middletown hotels with a pool

An indoor swimming pool with lounge chairs and a stone wall.
A Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.
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.

1. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
€107
includes taxes & fees
1 Nov - 2 Nov
Sleep Inn & Suites Middletown - Goshen
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
A gym with exercise equipment, treadmills, and weight machines.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

2. 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.
€98
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn by Hilton Middletown
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
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.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

3. 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.
€121
includes taxes & fees
4 Nov - 5 Nov
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
A modern bar area with a curved counter, bar stools, and a television screen.
A landscaped outdoor area with a fire feature, seating, and a pathway.
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.
€106
includes taxes & fees
28 Oct - 29 Oct
Courtyard by Marriott 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 hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A hotel room with two beds, a desk, a TV, and a chair.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

5. 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.
€119
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A swimming pool with four lounge chairs and a metal ladder.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.
A modern living room with a large TV, comfortable seating, and a patterned rug.

6. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
€124
includes taxes & fees
19 Oct - 20 Oct
Candlewood Suites Middletown Goshen by IHG
An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.
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.
A modern restaurant with a central island, multiple tables, and chairs.

7. 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.
€172
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Middletown
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.
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.
A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

8. 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.
€198
includes taxes & fees
1 Nov - 2 Nov
Residence Inn by Marriott Middletown Goshen
A rectangular swimming pool with a wooden deck and a fence.
A bathroom with a sink, mirror, towel rack, and toilet.
A Days Inn with a prominent sign, multiple motel units, and a well-maintained lawn.
A lobby with a reception desk, a Coca-Cola refrigerator, a Day's Inn sign, and a seating area with a chair and table.

9. Days Inn by Wyndham Middletown

Days Inn by Wyndham Middletown
New Hampton
  • Dive into summer bliss at this motel's seasonal outdoor pool, open June through August.
€81
includes taxes & fees
1 Nov - 2 Nov
Days Inn by Wyndham Middletown
An indoor swimming pool with a 9-foot depth warning.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.
A Simon Premium Outlet sign at Woodbury Commons.

10. 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.
€108
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express Hotel & Suites Chester by IHG
View all properties

Choose what matters most at hotels with a pool in Middletown

Breakfast included
Hot tub
4 stars
Spa
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 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.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
€121
includes taxes & fees
4 Nov - 5 Nov
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 modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A vending machine area with two beverage dispensers and a snack shelf stocked with various products.
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
€119
includes taxes & fees
3 Nov - 4 Nov
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A hotel room with a sofa, a television on a wooden stand, a bed, and a view of the hallway.
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.

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
€98
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn by Hilton Middletown
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.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
A conference room with multiple tables and chairs, a projector screen, and a green accent wall.

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
€172
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Middletown
A modern dining area with a large fish tank, sofas, and wooden tables and chairs.
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 Sleep Inn & Suites hotel with a stone facade, multiple balconies, and a covered entrance.

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
€107
includes taxes & fees
1 Nov - 2 Nov
Sleep Inn & Suites Middletown - Goshen
An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.
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.
A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
€198
includes taxes & fees
1 Nov - 2 Nov
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.
View all properties

Top Middletown Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"Very clean and friendly staff."
James 2-night trip
Posted 3 hours ago
Sleep Inn & Suites 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 1 day 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 some accommodation options with pools in Middletown?
Sleep Inn & Suites Middletown - Goshen: Features continental, an indoor pool and complimentary high-speed (wired) Internet access. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Offers buffet, an indoor pool and free self parking. Courtyard by Marriott Middletown Goshen: Provides spa services, an indoor pool and complimentary high-speed (wired) Internet access. Tru by Hilton Middletown: Offers daily, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. Hampton Inn by Hilton Middletown: Offers a snack bar/deli, an indoor pool and daily.
What is there to see and do in Middletown?
Explore places such as 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. Travellers love Middletown for its array of dining options.
When is the best time to book a hotel with a pool in Middletown?
Taking the local weather in Middletown into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Middletown are January, February, March and April, with each month seeing an average of 16 cm of snowfall.