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. Studio 6 Extended Stay Fishkill Route 9 NY : Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli. Overlook Lodge at Bear Mountain : Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Sonesta Simply Suites Nanuet : Features a snack bar/deli, a pool and free self parking. Sleep Inn & Suites Middletown - Goshen : Offers daily, an indoor pool and free self parking.

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Our top choices for Chester hotels with a pool

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

2 Jun - 3 Jun

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

3 Jun - 4 Jun

SpringHill Suites by Marriott Fishkill

Fishkill

Soak up relaxation at this family-friendly hotel with a pristine indoor pool for year-round swims.

includes taxes & fees

21 Jun - 22 Jun

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

14 Jun - 15 Jun

Harvest Inn

Pine Bush

Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.

includes taxes & fees

14 Jun - 15 Jun

Residence Inn by Marriott Fishkill

Fishkill

Discover the perfect indoor pool escape at Residence Inn Fishkill, where swimming meets fitness in a year-round aquatic sanctuary.

includes taxes & fees

7 Jun - 8 Jun

Hampton Inn Harriman Woodbury

Central Valley

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

includes taxes & fees

14 Jun - 15 Jun

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.

includes taxes & fees

21 Jun - 22 Jun

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Choose what matters most at hotels with a pool in Chester

Breakfast included

Hot tub

Top Chester Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

"We stayed overnight at the Lodge, as our daughter had her prom at the Inn. It was clean, peaceful, and affordable. My husband and I had a delicious dinner at the Inn restaurant and we all enjoyed breakfast at the Café. Lovely time."

The Crossroads Hotel, Newburgh

6/10 Okay

"Rooms have funky odor. Staff was great and changed me to another one but still felt the odd smell. There was lot of smoking and weed doing on the property and inside the hallways. The AC also not adjustable inside the room. It’s auto on and off. During the night time it would get hot and suddenly cold. No pool. No breakfast. Gym is there but not even water and proper weights are present. This property looks like had its glory once upon a time. But currently in a bad condition. It has lot of potential but needs the necessary up keeping. Needs lot of improvements."

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. Studio 6 Extended Stay Fishkill Route 9 NY: Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli. Overlook Lodge at Bear Mountain: Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Sonesta Simply Suites Nanuet: Features a snack bar/deli, a pool and free self parking. Sleep Inn & Suites Middletown - Goshen: 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 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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