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Find Hotels with a Pool in Chester, NY

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Check availability on Chester Hotels with a Pool

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Chester hotels with a pool

A Simon Premium Outlet sign at Woodbury Commons.

1. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.8 out of 10, Excellent, (1,002 reviews)
"Good place to stay."
United States
Stephanie
The price is SAR 364
SAR 448 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Hotel & Suites Chester by IHG
A swimming pool with a deck, surrounded by potted plants and outdoor furniture.

2. The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.6 out of 10, Exceptional, (240 reviews)
"The owners were so kind and attentive, and the grounds are absolutely beautiful! Delicious food, gorgeous mountain air, and the horses were adorable. Thank you for having us!"
United States
Sinead
The price is SAR 404
SAR 457 total
includes taxes & fees
11 Nov - 12 Nov
The Dominion House Bed & Breakfast
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

Quality Inn Spring Valley - Nanuet

Quality Inn Spring Valley - Nanuet

8/10 Good
"Everything good"
Darling 1-night trip
Posted 7 days ago
Quality Inn Spring Valley - Nanuet

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. 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. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Offers a snack bar/deli, an indoor pool, and buffet.
What is there to see and do in Chester?
Explore places like Woodbury Common Premium Outlets while you're in the area. Make a point to visit attractions like 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 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.