Find Hotels with a Pool in Pine Island, NY

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Check availability on Pine Island Hotels with a Pool

Our top choices for Pine Island hotels with a pool

Indoor pool
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1006)
"Great stay and room was very nice"
United States
Emmanuel
The price is AED 350
AED 430 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn Harriman Woodbury
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is AED 699
AED 1,272 total
includes taxes & fees
22 Dec - 23 Dec
LEGOLAND Hotel NEW York
Indoor pool, sun loungers
Holiday Inn Express Hotel & Suites Chester by IHG

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, (1003)
"The staff was excellent "
United States
Kelley
The price is AED 404
AED 477 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Chester by IHG
Indoor pool
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
3.0 star property
Middletown
8.6 out of 10, Excellent, (1002)
"The hotel was very clean, enjoyed my stay would recommend "
United States
Jessica
The price is AED 340
AED 402 total
includes taxes & fees
28 Dec - 29 Dec
Courtyard by Marriott Middletown Goshen
Seasonal outdoor pool
Fairfield Inn & Suites by Marriott Goshen Middletown

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, (1001)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is AED 356
AED 439 total
includes taxes & fees
24 Dec - 25 Dec
Fairfield Inn & Suites by Marriott Goshen Middletown
Indoor pool
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen
2.5 star property
Middletown
8.6 out of 10, Excellent, (1002)
"Love this hotel "
United States
Jennifer
The price is AED 368
AED 435 total
includes taxes & fees
11 Jan - 12 January 2026
Sleep Inn & Suites Middletown - Goshen
Seasonal outdoor pool
Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro

Days Inn by Wyndham Wurtsboro
2.0 star property
Wurtsboro
7.6 out of 10, Good, (593)
"I love "
United States
Niralkumar
The price is AED 364
AED 411 total
includes taxes & fees
2 Jan - 3 January 2026
Days Inn by Wyndham Wurtsboro
Indoor pool
La Quinta Inn & Suites by Wyndham Middletown-Goshen

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, (936)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
The price is AED 443
AED 524 total
includes taxes & fees
21 Dec - 22 Dec
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Indoor pool, sun loungers
Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford

Best Western Hunt's Landing Hotel Matamoras/Milford
3.0 star property
Matamoras
8.4 out of 10, Very Good, (1000)
"Friendly staff, nice and clean room and breakfast area."
United States
Jean
The price is AED 334
AED 364 total
includes taxes & fees
21 Dec - 22 Dec
Best Western Hunt's Landing Hotel Matamoras/Milford
Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"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
17 Dec - 18 Dec
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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Top Pine Island Hotel Reviews

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"The staff was excellent "
Kelley 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Chester by IHG

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Frequently asked questions

What are some accommodations with pools in Pine Island?
Hampton Inn Harriman Woodbury: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Offers daily, an indoor pool, and free self parking. Sleep Inn & Suites Monroe - Woodbury: Features continental, an indoor pool, and complimentary wired internet access. Sleep Inn & Suites Middletown - Goshen: Hotel located near LEGOLAND® New York. Offers on-the-go, a pool, and complimentary wired internet access. Holiday Inn Express Hotel & Suites Chester by IHG: Features daily, a seasonal outdoor pool, and complimentary wired internet access.
What is there to see and do in Pine Island?
Surround yourself with nature at Pine Island Town Park. Discover sights such as Scenic Farms Golf Course during your stay.
When is the best time to book a hotel with a pool in Pine Island?
You may want to consider a place to stay with an outdoor swimming pool if you plan to visit Pine Island in the warmest months of July, August, or June when the average temperature is 69°F. Lodging with an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 32°F.