TOP Hotels with Pool in Highland Mills, NY for 2026

Q: What are some accommodation options with pools in Highland Mills?

Sleep Inn & Suites Middletown - Goshen : Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Hyatt Place Poughkeepsie / Hudson Valley : Offers a snack bar/deli, an indoor pool and free self parking. Spark by Hilton Fishkill : Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Overlook Lodge at Bear Mountain : Offers a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet : Offers daily, an indoor pool and free self parking.

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Our top choices for Highland Mills hotels with a pool

Hampton Inn Harriman Woodbury

Central Valley

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

Rp2.882.141 total

includes taxes & fees

5 Aug - 6 Aug

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

Rp2.179.116 total

includes taxes & fees

5 Aug - 6 Aug

Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG

Peekskill

Luxurious indoor pool sanctuary offers year-round aquatic relaxation while overlooking Hudson Valley's scenic landscapes.

Rp2.433.188 total

includes taxes & fees

26 Jul - 27 Jul

Home2 Suites by Hilton Middletown

Middletown

Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.

Rp4.319.920 total

includes taxes & fees

11 Aug - 12 Aug

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.

Rp2.754.956 total

includes taxes & fees

16 Aug - 17 Aug

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.

Rp2.284.968 total

includes taxes & fees

3 Aug - 4 Aug

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.

Rp2.493.408 total

includes taxes & fees

16 Aug - 17 Aug

Hampton Inn by Hilton Middletown

Middletown

Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.

Rp2.061.885 total

includes taxes & fees

11 Aug - 12 Aug

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Choose what matters most at hotels with a pool in Highland Mills

Breakfast included

4 stars

Top Highland Mills Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent

"Great staff and cleanliness."

Overlook Lodge at Bear Mountain

8/10 Good

"I was in the area for a lacrosse camp and stayed in the cottages. The lodge is conveniently located near the Bear Mountain Bridge that’s takes you across the Hudson to quaint towns and local attractions. A drive past the lodge, up to Perkins point, is peaceful and has beautiful views. The area is breathtaking! The U.S. Military Academy at West Point is an easy 10 minute drive away and has to be the most historically intriguing and incredible looking base in the world. I didn’t spend a lot of time at my cottage but the employees were responsive, the beds were comfortable, the location was great and the food at the restaurant was top notch!"

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."

Frequently asked questions

What are some accommodation options with pools in Highland Mills?

Sleep Inn & Suites Middletown - Goshen: Features continental, an indoor pool and complimentary high-speed (wired) Internet access. Hyatt Place Poughkeepsie / Hudson Valley: Offers a snack bar/deli, an indoor pool and free self parking. Spark by Hilton Fishkill: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool and a snack bar/deli. Overlook Lodge at Bear Mountain: Offers a snack bar/deli, a pool and free self parking. DoubleTree by Hilton Hotel Nanuet: Offers daily, an indoor pool and free self parking.

What is there to see and do in Highland Mills?

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 Arrow Park Lake and Lodge and Storm King Art Center.

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

You may want to think about a place to stay with an outdoor swimming pool if you'll be visiting Highland Mills in the warmest months of July, August or June, when the average temperature is 21°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or December, when the average temp is 0°C.

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