Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Tonight
27 Mar - 28 Mar
Tomorrow
28 Mar - 29 Mar
This weekend
27 Mar - 29 Mar
Next weekend
3 Apr - 5 Apr

Our top choices for Chester hotels with a pool

Indoor pool, sun loungers

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1,002 reviews)
"We have been several times during the past few years the hotel is in very good condition and the coffee is really good available 24 hours a day the breakfast has several choices that are good the rooms are clean the A/C and heat work great overall great place to stay we come sometimes for a quick weekend getaway from New York City will continue to come back. Great local diner and restaurants."
United States
Kenneth
The price is AED 386
AED 456 total
includes taxes & fees
1 Apr - 2 Apr
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233 reviews)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is AED 790
AED 893 total
includes taxes & fees
6 Apr - 7 Apr
The Dominion House Bed & Breakfast
Indoor pool

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1,010 reviews)
"Great stay!!! "
United States
diana
The price is AED 400
AED 473 total
includes taxes & fees
29 Mar - 30 Mar
Courtyard by Marriott Middletown Goshen
Seasonal outdoor pool

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain
2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1,001 reviews)
"Great staff and clean rooms. Beautiful views."
United States
Renee
The price is AED 341
AED 386 total
includes taxes & fees
29 Mar - 30 Mar
Overlook Lodge at Bear Mountain
Seasonal outdoor pool

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (612 reviews)
"Everything was clean. "
United States
John
The price is AED 331
AED 374 total
includes taxes & fees
29 Mar - 30 Mar
Days Inn by Wyndham Wurtsboro
Seasonal outdoor pool

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
8.8 out of 10, Excellent, (1,000 reviews)
"Amazing staff Great breakfast Clean quiet rooms"
United States
R
The price is AED 434
AED 534 total
includes taxes & fees
12 Apr - 13 Apr
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool

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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1,000 reviews)
"Superb place to stay."
United States
Denessy
The price is AED 350
AED 396 total
includes taxes & fees
12 Apr - 13 Apr
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
BBQ/picnic area

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"It was a beautiful experience. Clean and 5 star service. The staff so friendly and helpful. Peaceful fun experience. "
United States
Amanda
The price is AED 342
AED 404 total
includes taxes & fees
31 Mar - 1 Apr
Hampton Inn by Hilton Middletown
Indoor pool

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1,000 reviews)
"A good place to stay when you are in this region. "
Canada
Valere
The price is AED 411
AED 475 total
includes taxes & fees
31 Mar - 1 Apr
Hilton Garden Inn Fishkill
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is AED 373
AED 754 total
includes taxes & fees
29 Mar - 30 Mar
Historic Cabin with Pool & Fire Pit
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chester

Breakfast included
Hot tub

Top Chester Hotel Reviews

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

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

8/10 Good
"Convenient, clean and friendly.. "
Terry 1-night trip
Posted 7 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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Frequently asked questions

What are some accommodations 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 wired internet access. DoubleTree by Hilton Hotel Nanuet: Offers a snack bar/deli, a pool, and free self parking. Sonesta Simply Suites Nanuet: Features continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers daily, an indoor pool, and complimentary wired internet access. Hampton Inn Harriman Woodbury: Features complimentary wired internet access, an indoor pool, and free self parking.
What is there to see and do in Chester?
Make a point to visit attractions like The Rock Sports Complex and Castle Fun Center. Discover sights such as Museum Village and Goosepond Mountain State Park during your stay. 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 think about a place to stay that offers an outdoor pool if you plan to visit Chester in the warmest months of July, August, or June when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 32°F.