Hotels with Swimming Pool in Chester, New York

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Check availability on Chester Hotels with Swimming 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)
  • cleanliness
    Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
"Kid enjoyed the pool."
United States
Petko
The price is P6,666
P8,207 total
includes taxes & fees
May 25 - May 26
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)
  • cleanliness
    Dive into summer fun at this bed & breakfast's refreshing outdoor pool, surrounded by garden views.
"The breakfast was delicious and filling. The pool and hot tub were clean and refreshing. The hospitality and house was just what we needed. We loved it!"
United States
Laura
The price is P13,253
P14,992 total
includes taxes & fees
May 18 - May 19
The Dominion House Bed & Breakfast

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.4 out of 10, Very Good, (1,011 reviews)
  • cleanliness
    Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
"we loved the indoor pool highly recommend"
United States
Kristen
The price is P7,030
P8,304 total
includes taxes & fees
Jun 10 - Jun 11
Courtyard by Marriott Middletown Goshen

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
"Pool was clean."
United States
Jeanne
The price is P6,464
P7,635 total
includes taxes & fees
Jun 2 - Jun 3
Hampton Inn by Hilton Middletown

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (41 reviews)
  • cleanliness
    Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.
"Kids loved it"
Canada
Mathieu
The price is P18,618
P29,483 total
includes taxes & fees
May 28 - May 29
LEGOLAND Hotel NEW York

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)
  • cleanliness
    Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.
"The swimming pool was clean and so great!"
United States
Maria
The price is P10,431
P12,843 total
includes taxes & fees
May 26 - May 27
Overlook Lodge at Bear Mountain

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, (1,008 reviews)
  • cleanliness
    Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.
"The boys loved the pool!"
United States
Sherry
The price is P6,054
P6,849 total
includes taxes & fees
May 31 - Jun 1
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (618 reviews)
  • cleanliness
    Take a dip in the seasonal outdoor pool, a refreshing retreat with mountain views.
"The room was average yet clean. Small clean pool. However, the desk clerk charged my checking account when I had already paid hotels.com 355$ charge on top of prepay fee. Training required as I gave him the it# and said it is prepaid. Disappointed in the poor training that limited my spending money because he didn't do his job correctly. Hotels.com handled this well and my 355$ should be back in my account soon. "
United States
Anonymous traveler
The price is P6,604
P7,463 total
includes taxes & fees
May 25 - May 26
Days Inn by Wyndham Wurtsboro

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
3.0 star property
Goshen
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
"Comfortable beds, coffee and tea available, nice pool."
Canada
Veronique
The price is P8,579
P10,563 total
includes taxes & fees
May 25 - May 26
Fairfield Inn & Suites by Marriott Goshen Middletown

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Comfort suites with indoor pool oasis makes relaxation a year-round affair in Fishkill.
"N kids enjoyed the pool."
United States
Maiesha
The price is P6,396
P7,395 total
includes taxes & fees
Jun 10 - Jun 11
Comfort Suites Fishkill near Interstate 84
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.

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

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

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