Chester Hotels with Pool, New York: Chester Hotel Guide

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

Holiday Inn Express Hotel & Suites Chester by IHG : Hotel located near LEGOLAND® New York. Features on-the-go, a pool and complimentary high-speed (wired) Internet access. Overlook Lodge at Bear Mountain : Hotel, 1-minute walk from Bear Mountain State Park. Offers 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. Sleep Inn & Suites Middletown - Goshen : 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 Chester hotels with a pool

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

includes taxes & fees

5 Aug - 6 Aug

The Dominion House Bed & Breakfast

Chester

Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.

includes taxes & fees

20 Jul - 21 Jul

Overlook Lodge at Bear Mountain

Bear Mountain

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

includes taxes & fees

16 Jul - 17 Jul

Hampton Inn by Hilton Middletown

Middletown

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

includes taxes & fees

12 Aug - 13 Aug

Days Inn by Wyndham Wurtsboro

Wurtsboro

Take a dip in the seasonal outdoor pool, a refreshing retreat with mountain views.

includes taxes & fees

16 Jul - 17 Jul

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.

includes taxes & fees

26 Jul - 27 Jul

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.

includes taxes & fees

26 Jul - 27 Jul

Courtyard by Marriott Middletown Goshen

Middletown

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

includes taxes & fees

12 Aug - 13 Aug

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Breakfast included

Hot tub

Top Chester Hotel Reviews

Crowne Plaza Suffern - Mahwah by IHG

10/10 Excellent

"Friendly staff, super clean and updated room. The beds were so comfortable. The lobby and bar are beautiful and airy. If you are given the option to purchase the in-house breakfast, it is a great deal! The food selection was fantastic and everything was delicious and fresh. We always love staying at this property and look forward to staying again soon."

DoubleTree by Hilton Hotel Nanuet

8/10 Good

"The room was clean , but worn, headboard clearly discolored from wear and tear, cracked sink, shower faucet drip, a strange scratching grinding noise in the wall next to the bed. at night. The location suited our purpose for 3 nights visiting relatives in New City. Staff were responsive to our requests. Appeared safe. 3 stars"

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."

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 Chester?

Holiday Inn Express Hotel & Suites Chester by IHG: Hotel located near LEGOLAND® New York. Features on-the-go, a pool and complimentary high-speed (wired) Internet access. Overlook Lodge at Bear Mountain: Hotel, 1-minute walk from Bear Mountain State Park. Offers 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. Sleep Inn & Suites Middletown - Goshen: 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 Chester?

Explore places such as LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions such as The Rock Sports Complex and Castle Fun Center. The restaurants and shopping are just some of the things to enjoy while you're in the area.

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

You may want to consider a place to stay that has an outdoor pool if you plan to visit Chester in the hottest months of July, August or June, when the average temp is 21°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temperature is 0°C.

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Our top choices for Chester hotels with a pool