The Best Hotels with a Pool in Montgomery, NY from ₩172,573 in 2026

Q: What are some accommodations 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 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.

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Our top choices for Montgomery hotels with a pool

Sun Retreats Birchwood Acres

Greenfield Park

₩999,278 total

includes taxes & fees

Jul 16 - Jul 17

Hampton Inn Harriman Woodbury

Central Valley

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

₩240,380 total

includes taxes & fees

Jul 21 - Jul 22

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

₩181,434 total

includes taxes & fees

Aug 5 - Aug 6

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.

₩200,815 total

includes taxes & fees

Aug 2 - Aug 3

Sleep Inn & Suites Middletown - Goshen

Middletown

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

₩215,635 total

includes taxes & fees

Aug 2 - Aug 3

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.

₩172,573 total

includes taxes & fees

Aug 9 - Aug 10

Comfort Suites Fishkill near Interstate 84

Fishkill

Comfort suites with indoor pool oasis makes relaxation a year-round affair in Fishkill.

₩199,359 total

includes taxes & fees

Aug 10 - Aug 11

Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Splash into year-round relaxation at this hotel's indoor swimming oasis, just minutes from Algonquin Park and local attractions.

₩215,765 total

includes taxes & fees

Jul 26 - Jul 27

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Choose what matters most at hotels with a pool in Montgomery

Breakfast included

Hot tub

Top Montgomery Hotel Reviews

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

10/10 Excellent

"Nice stay"

Overlook Lodge at Bear Mountain

10/10 Excellent

"I wish I’d stayed for a week so I could’ve hiked and swam in the lake. Instead, I was there for a weekend so we took advantage of the bar and the silence of the woods by simply walking through. The staff we met were wonderful: Sean at check-in is gregarious and kind; Beth in the bar is efficient and friendly, as were both bartenders named Mike."

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 accommodations 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 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 like 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 into account the local weather in Montgomery is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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