TOP Hotels with Pool in Montgomery, NY for 2026

Q: What are some accommodation options with pools in Montgomery?

Super 8 by Wyndham Montgomery Maybrook : Hotel steps from The Kartrite Resort & Indoor Waterpark. Provides a children's pool, an indoor pool and a water park. Holiday Inn Express & Suites Montgomery by IHG : Features a snack bar/deli, an indoor pool and free self parking. The Kartrite Resort & Indoor Waterpark : Hotel, 4-minute walk from Resorts World Catskills. Features 6 restaurants, a pool and a full-service spa. Hyatt Place Poughkeepsie / Hudson Valley : Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Spark by Hilton Fishkill : Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli.

Two large silos, a barn, and a green field under a blue sky.

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Our top choices for Montgomery hotels with a pool

Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Dive into serenity at this indoor pool sanctuary with hydromassage showers and a firepit for year-round relaxation.

Rp2.694.547 total

includes taxes & fees

13 Jul - 14 Jul

Hampton Inn Harriman Woodbury

Central Valley

Splash into year-round luxury at this indoor pool retreat just steps from premium shopping outlets.

Rp3.105.397 total

includes taxes & fees

2 Aug - 3 Aug

Courtyard by Marriott Middletown Goshen

Middletown

Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.

Rp2.530.029 total

includes taxes & fees

27 Jul - 28 Jul

Sleep Inn & Suites Middletown - Goshen

Middletown

Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.

Rp2.624.247 total

includes taxes & fees

2 Aug - 3 Aug

The Kartrite Resort & Indoor Waterpark

Monticello

Splash into four-season aquatic fun at this family paradise with both indoor and outdoor pool playgrounds.

Rp7.411.270 total

includes taxes & fees

15 Jul - 16 Jul

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.

Rp2.270.623 total

includes taxes & fees

26 Jul - 27 Jul

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Splash into year-round swimming at this hotel near Vassar College with indoor pool sanctuary.

Rp3.241.875 total

includes taxes & fees

12 Jul - 13 Jul

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

New Windsor

Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.

Rp2.100.310 total

includes taxes & fees

26 Jul - 27 Jul

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Choose what matters most at hotels with a pool in Montgomery

Breakfast included

Hot tub

Top Montgomery Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent

"Nice Hotel - Perfect for a one night stay. Room was very clean, staff was very professional & polite, & there was ample parking. The biggest surprise for me was the complimentary breakfast. I expected a scaled down continental grab a bite & go. However, it was much better than that!! A nice variety of breakfast items - all fresh & really good. The breakfast space was ultra clean & was very organized!! Will gladly go back again!!"

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"Our room was really clean. The pullout bed didn’t have linen on it but housekeeping came rather quickly at 10:30pm and gave it to us. The free breakfast was really good. All the staff were really friendly. The pool was a little cloudy. But overall we enjoyed our stay here and would stay again. It’s only 7 minutes from LegoLand and we paid less than half the price of the resort."

Frequently asked questions

What are some accommodation options with pools in Montgomery?

Super 8 by Wyndham Montgomery Maybrook: Hotel steps from The Kartrite Resort & Indoor Waterpark. Provides a children's pool, an indoor pool and a water park. Holiday Inn Express & Suites Montgomery by IHG: Features a snack bar/deli, an indoor pool and free self parking. The Kartrite Resort & Indoor Waterpark: Hotel, 4-minute walk from Resorts World Catskills. Features 6 restaurants, a pool and a full-service spa. Hyatt Place Poughkeepsie / Hudson Valley: Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Spark by Hilton Fishkill: Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli.

What is there to see and do in Montgomery?

Explore places such as LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. The picturesque setting of Orange County Arboretum and Thomas Bull Memorial Park showcase the area's natural beauty. You'll also discover lots of options for restaurants in Montgomery.

When is the best time to book a hotel with a pool in Montgomery?

Taking the local weather in Montgomery 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 0°C. The snowiest months in Montgomery are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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