Find Hotels with a Pool in Chester, NY

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

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, (1,001 reviews)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is AED 298
AED 351 total
includes taxes & fees
28 Jan - 29 Jan
Holiday Inn Express Hotel & Suites Chester by IHG

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
26 Jan - 27 Jan
The Dominion House Bed & Breakfast

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet
4.0 star property
Nanuet
9.0 out of 10, Wonderful, (1,045 reviews)
"Clean room, helpful staff and good bar/restaurant "
United States
Stephen
The price is AED 373
AED 435 total
includes taxes & fees
22 Feb - 23 Feb
DoubleTree by Hilton Hotel Nanuet

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)
"The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price."
United States
Judith
The price is AED 363
AED 410 total
includes taxes & fees
4 Feb - 5 Feb
Overlook Lodge at Bear Mountain

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,000 reviews)
"Clean Rooms, clean hotel overall. Plenty of parking."
United States
KenNETH
The price is AED 297
AED 350 total
includes taxes & fees
29 Jan - 30 Jan
Hampton Inn by Hilton Middletown

HYATT house Fishkill/Poughkeepsie

HYATT house Fishkill/Poughkeepsie
3.0 star property
Fishkill
8.8 out of 10, Excellent, (1,002 reviews)
"Everything was great"
United States
Ann
The price is AED 403
AED 456 total
includes taxes & fees
24 Jan - 25 Jan
HYATT house Fishkill/Poughkeepsie

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1,005 reviews)
"Room was clean,Staff was very friendly and helpful "
United States
Antonio
The price is AED 337
AED 381 total
includes taxes & fees
2 Feb - 3 Feb
Hilton Garden Inn Fishkill

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (963 reviews)
"GREAT STAY, CLEAN HOTEL AND ROOM, GREAT POOL AND HOT TUB GYM IS CLEAN LOVED IT"
United States
NICOLE
The price is AED 403
AED 476 total
includes taxes & fees
1 Feb - 2 Feb
La Quinta Inn & Suites by Wyndham Middletown-Goshen

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (1,000 reviews)
"Yes stay was pleasant "
United States
henry
The price is AED 343
AED 389 total
includes taxes & fees
29 Jan - 30 Jan
Comfort Suites Fishkill near Interstate 84

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1,002 reviews)
"Clean room, breakfast was plentiful and front desk were great."
United States
Robert
The price is AED 342
AED 421 total
includes taxes & fees
29 Jan - 30 Jan
Fairfield Inn & Suites by Marriott Goshen Middletown
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.

Top Chester Hotel Reviews

Explore a world of travel with Expedia

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: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Offers daily, an indoor pool, and complimentary wired internet access. Crowne Plaza Suffern - Mahwah by IHG: Offers continental, an indoor pool, and complimentary wired internet access. Hampton Inn Harriman Woodbury: Provides a full-service spa, a seasonal outdoor pool, and a snack bar/deli.
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 Goosepond Mountain State Park and Museum Village 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.