TOP Hotels with Pool in New Windsor, NY for 2026

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Our top choices for New Windsor hotels with a pool

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.

Rp2.093.011 total

includes taxes & fees

26 Jul - 27 Jul

Homewood Suites Stewart Airport

New Windsor

Dive into blissful relaxation at this hotel's indoor pool oasis with bubbling hot tub escape.

Rp5.125.696 total

includes taxes & fees

17 Jul - 18 Jul

Seasonal outdoor pool, pool umbrellas, pool loungers

LEGOLAND Hotel NEW York

Goshen

Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.

Rp8.602.724 total

includes taxes & fees

3 Aug - 4 Aug

Overlook Lodge at Bear Mountain

Bear Mountain

Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.

Rp3.758.965 total

includes taxes & fees

13 Jul - 14 Jul

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

Rp2.262.731 total

includes taxes & fees

26 Jul - 27 Jul

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.

Rp3.202.925 total

includes taxes & fees

20 Jul - 21 Jul

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

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

Rp3.230.607 total

includes taxes & fees

12 Jul - 13 Jul

Hampton Inn Harriman Woodbury

Central Valley

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

Rp2.980.625 total

includes taxes & fees

19 Jul - 20 Jul

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Breakfast included

Hot tub

Top New Windsor Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

8/10 Good

"Nice staff. Clean room. Safe parking."

Inn on the Hudson

8/10 Good

"I booked two rooms for me, my adult daughter and her two teen daughters, one teen son, and my daughter's two dogs, for my grandson's graduation from Air Assault school at West Point. Each room had two double beds. The rooms were generally clean, but worn. The air conditioning worked noisily but well, which was important for the early July weather. My room had water on the floor upon arrival next to the refrigerator, but an extra towel quickly took care of that. The water was due to the refrigerator freezer defrosting because it was turned off prior to our arrival. Bed and bathroom linens were clean and a check of the beds revealed no surprises. The free breakfast was mostly some hard boiled eggs, breakfast cereal, and make your own waffles. I asked about water and was told the bathroom sinks had some. There was a vending machine with drinks and snacks in the lobby area adjacent to the breakfast stuff. In case it's not clear, the pool has been closed for years. There was a $50 charge for each dogs per day, which I knew was coming, so I was not surprised. I was thankful they allowed them. I did not detect any bad smells in our room which sometimes happens with pet-friendly hotels. The lack of bad smells is probably due to the fact that the floors are wood or lvp tile, not carpet. Water pressure and temperature was good for showers. The bathtub lining was cracked/peeling up in a few areas, but not horrible. All in all, not the greatest, but I don't regret staying there."

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 New Windsor?

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point: Features free self parking, an indoor pool and complimentary wireless Internet access. Homewood Suites Stewart Airport: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. Hyatt Place Poughkeepsie / Hudson Valley: Provides a snack bar/deli, an indoor pool and free self parking. Overlook Lodge at Bear Mountain: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Spark by Hilton Fishkill: Features continental, an indoor pool and complimentary high-speed (wired) Internet access.

What is there to see and do in New Windsor?

Explore places such as Woodbury Common Premium Outlets and LEGOLAND® New York while you're in the area. Make a point to visit attractions such as Canopus Beach and Algonquin Park. Travellers love New Windsor for its array of dining options.

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

You may want to think about accommodation with an outdoor swimming pool if you plan to visit New Windsor in the warmest months of July, August or June, when the average temperature is 21°C. Accommodation offering an indoor pool may be what you want if you are visiting during the coldest months of January, February or December, when the average temperature is 0°C.

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Our top choices for New Windsor hotels with a pool

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

Homewood Suites Stewart Airport

LEGOLAND Hotel NEW York

Overlook Lodge at Bear Mountain

Holiday Inn Express Hotel & Suites Chester by IHG

Fairfield Inn & Suites by Marriott Goshen Middletown

Home2 Suites By Hilton Poughkeepsie

Hampton Inn Harriman Woodbury

Hampton Inn by Hilton New Paltz

Brinckerhoff Inn

Choose what matters most at hotels with a pool in New Windsor

Top New Windsor Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Sleep Inn & Suites Middletown - Goshen

Americas Best Value Inn New Paltz

Inn on the Hudson

Holiday Inn Express Hotel & Suites Chester by IHG

Overlook Lodge at Bear Mountain

Ramada by Wyndham Newburgh/West Point

Frequently asked questions

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Search Hotels with Pool in New Windsor

Change your mind

Treat yourself

Be picky

Check availability on New Windsor Hotels with Pool

Our top choices for New Windsor hotels with a pool

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

Homewood Suites Stewart Airport

LEGOLAND Hotel NEW York

Overlook Lodge at Bear Mountain

Holiday Inn Express Hotel & Suites Chester by IHG

Fairfield Inn & Suites by Marriott Goshen Middletown

Home2 Suites By Hilton Poughkeepsie

Hampton Inn Harriman Woodbury

Hampton Inn by Hilton New Paltz

Brinckerhoff Inn

Choose what matters most at hotels with a pool in New Windsor

Top New Windsor Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Frequently asked questions

Explore a world of travel with Expedia