Beautiful Autumn View in Bear Mountain State Park

Find Hotels with a Pool in Middletown, NY from CA $159

  • 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 a Pool

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Middletown hotels with a pool

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.
A landscaped outdoor area with a fire feature, seating, and a pathway.

1. 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.
CA $140
CA $165 total
includes taxes & fees
Sep 7 - Sep 8
Courtyard by Marriott Middletown Goshen
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
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.

2. 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.
CA $169
CA $200 total
includes taxes & fees
Aug 30 - Aug 31
La Quinta Inn & Suites by Wyndham 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 Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

3. 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.
CA $135
CA $159 total
includes taxes & fees
Sep 21 - Sep 22
Hampton Inn by Hilton Middletown
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.

4. Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
Middletown
  • Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.
CA $152
CA $180 total
includes taxes & fees
Sep 21 - Sep 22
Sleep Inn & Suites Middletown - Goshen
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.

5. 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.
CA $169
CA $199 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with four lounge chairs and a metal ladder.
A hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.
A swimming pool with clear blue water, tiled walls, and a tiled floor.

6. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
CA $176
CA $208 total
includes taxes & fees
Aug 31 - Sep 1
Candlewood Suites Middletown Goshen by IHG
An indoor swimming pool with multiple lounge chairs and tables, surrounded by large windows.
A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern design with brick and beige facades, and a parking lot in front.
A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern brick facade and multiple windows.
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.
CA $237
CA $285 total
includes taxes & fees
Sep 20 - Sep 21
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.
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.
A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

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.
CA $273
CA $322 total
includes taxes & fees
Sep 7 - Sep 8
Residence Inn by Marriott Middletown Goshen
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 Simon Premium Outlet sign at Woodbury Commons.
A modern hotel lobby with a large map mural, seating areas, and a reception desk.

9. 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.
CA $147
CA $181 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express Hotel & Suites Chester by IHG
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
A modern restaurant with a long counter, wooden chairs, and pendant lighting.
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.

10. 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.
CA $185
CA $228 total
includes taxes & fees
Sep 13 - Sep 14
Fairfield Inn & Suites by Marriott Goshen Middletown
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 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.
A vending machine area with two beverage dispensers and a snack shelf stocked with various products.

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
CA $169
CA $200 total
includes taxes & fees
Aug 30 - Aug 31
La Quinta Inn & Suites by Wyndham Middletown-Goshen
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
CA $152
CA $180 total
includes taxes & fees
Sep 21 - Sep 22
Sleep Inn & Suites 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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
CA $135
CA $159 total
includes taxes & fees
Sep 21 - Sep 22
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.

Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
CA $169
CA $199 total
includes taxes & fees
Aug 30 - Aug 31
Holiday Inn Express & Suites Middletown - Goshen by IHG
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern design with brick and beige facades, and a parking lot in front.
An indoor swimming pool with multiple lounge chairs and tables, surrounded by large windows.
A multi-story hotel building with a prominent 'HOME 2' sign, featuring a modern brick facade and multiple windows.

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
CA $237
CA $285 total
includes taxes & fees
Sep 20 - Sep 21
Home2 Suites by Hilton Middletown
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 spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.
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.

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
Middletown
CA $273
CA $322 total
includes taxes & fees
Sep 7 - Sep 8
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

10/10 Excellent
"Great stay"
Rebecca 2-night trip
Posted 1 hour ago
Sleep Inn & Suites Middletown - Goshen
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

10/10 Excellent
"Good affordable room"
Adonis 1-night trip
Posted 3 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"The staff was excellent. They helped with a few challenges that we had while we stayed there for our daughter's wedding. Yankee, one of the managers, is a reason that we will be going back there again next year!"
Rich 4-night trip
Posted 10 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

8/10 Good
"No cabinets for clothes…for our stay it was ok because our stay is just one night…"
Alejandro 1-night trip
Posted 2 days ago
Hampton Inn by Hilton Middletown

Frequently asked questions

What are the best hotels in Middletown with outdoor pools?
If you're looking for a refreshing stay in Middletown, the Holiday Inn Express & Suites Middletown - Goshen by IHG is a fantastic option. This hotel features a lovely outdoor pool area, superb for families seeking relaxation and fun in the sun. Guests rave about the cleanliness of the rooms and the friendliness of the staff, making it a welcoming choice. Plus, you can enjoy a complimentary breakfast that many travellers have described as great, alongside free WiFi and convenient self-parking.Another excellent choice is the Hampton Inn by Hilton Middletown, which also boasts an outdoor pool. Families appreciate the spacious and clean rooms, as well as the fresh breakfast provided each morning at no extra charge. With its convenient yet quiet location, this hotel offers a peaceful retreat, alongside free amenities like WiFi and toiletries, ensuring a comfortable stay for everyone.Both of these hotels have received commendable reviews, with the Holiday Inn Express rated 8.8 and the Hampton Inn at 8.6, reflecting the quality service and experience you can expect during your visit.
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 CA $159 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 Galleria at Crystal Run?
The Hampton Inn by Hilton Middletown is an excellent choice for travellers seeking a hotel with an outdoor pool near Galleria at Crystal Run. With an excellent traveller rating of 8.6, this hotel provides a welcoming environment that families appreciate.Guests rave about the spacious and clean rooms, making it a comfortable base for your adventures. The outdoor pool is described as nice and well-maintained, superb for a refreshing dip after a day of shopping or exploring.Additionally, the Hampton Inn offers a variety of convenient amenities that enhance your stay. Enjoy complimentary WiFi, free self-parking, and a delicious free continental breakfast that guests often mention as fresh and satisfying. Families traveling with young children will benefit from the availability of cribs at no extra charge.
Is it cheaper to book flights and a hotel in Middletown 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 travel 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 with an outdoor pool in Middletown for you.
How can I save on a hotel in Middletown with Expedia?
Before booking your Middletown hotel, remember to join One Key™, Expedia's free travel rewards program. Just sign up and sign in to access instant discounts with Member Prices as well as member-only perks. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.

Explore a world of travel with Expedia