The Best Hotels with a Pool in Highland, NY from ₩175,252 in 2026

Q: What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie : Features a snack bar/deli, an indoor pool, and free self parking. Best Western Plus Kingston Hotel And Conference Center : Offers a full-service spa, a seasonal outdoor pool, and 3 bars. Studio 6 Extended Stay Fishkill Route 9 NY : Offers a snack bar/deli, an indoor pool, and buffet. Hyatt Place Poughkeepsie / Hudson Valley : Features a snack bar/deli, an indoor pool, and buffet. Wildflower Farms, Auberge Collection : Features buffet, an indoor pool, and complimentary wired internet access.

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Our top choices for Highland hotels with a pool

Hyatt Place Poughkeepsie / Hudson Valley

Crown Heights

Dive into serenity at this indoor pool sanctuary with hydromassage showers and a firepit for year-round relaxation.

₩177,130 total

includes taxes & fees

Jun 2 - Jun 3

Hampton Inn & Suites Poughkeepsie

Crown Heights

Family-friendly hotel features a clean, warm pool with ample towels for a serene, refreshing retreat.

₩185,238 total

includes taxes & fees

Jun 15 - Jun 16

Hampton Inn & Suites Newburgh Stewart Airport

Newburgh

Splash into year-round relaxation at this hotel's indoor swimming oasis, just minutes from Algonquin Park and local attractions.

₩203,036 total

includes taxes & fees

Jun 2 - Jun 3

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

New Windsor

Dive into this indoor pool oasis with aquatic fun that awaits year-round, just minutes from Stewart Airport and West Point.

₩179,602 total

includes taxes & fees

Jun 21 - Jun 22

Hilton Garden Inn Fishkill

Fishkill

Indoor pool sanctuary with year-round swimming and 24-hour fitness center enhances this hotel in the business district.

₩227,335 total

includes taxes & fees

Jun 10 - Jun 11

Comfort Suites Fishkill near Interstate 84

Fishkill

Comfort suites with indoor pool oasis makes relaxation a year-round affair in Fishkill.

₩175,252 total

includes taxes & fees

Jun 21 - Jun 22

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

Splash into year-round swimming at this hotel near Vassar College with indoor pool sanctuary.

₩199,651 total

includes taxes & fees

Jun 22 - Jun 23

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Fishkill

Swim under indoor skylights as the hot tub bubbles nearby at this relaxing poolside escape.

₩233,646 total

includes taxes & fees

May 31 - Jun 1

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Choose what matters most at hotels with a pool in Highland

Breakfast included

Hot tub

Top Highland Hotel Reviews

Residence Inn by Marriott Kingston

10/10 Excellent

"The room was very nice. An urgent matter came up at home and I wasn’t able to spend the night. But what little time I was there it was nice"

Courtyard by Marriott Poughkeepsie

8/10 Good

"This is a clean, well-situated facility. Comfortable bed and friendly staff. Note that there is a $10 fee to park your vehicle and breakfast is not included, though it's available on the premises for a fee. There is only one mirror in the room and it's over the sink. How about upgrading the hairdryer; it's got to be at least 15 years old! The place itself is reasonably priced. While bottled water is in the room for the coffee maker, it'll cost you $5 to use the water - tap water works for me and it's free!"

Frequently asked questions

What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie: Features a snack bar/deli, an indoor pool, and free self parking. Best Western Plus Kingston Hotel And Conference Center: Offers a full-service spa, a seasonal outdoor pool, and 3 bars. Studio 6 Extended Stay Fishkill Route 9 NY: Offers a snack bar/deli, an indoor pool, and buffet. Hyatt Place Poughkeepsie / Hudson Valley: Features a snack bar/deli, an indoor pool, and buffet. Wildflower Farms, Auberge Collection: Features buffet, an indoor pool, and complimentary wired internet access.

What is there to see and do in Highland?

The picturesque setting of Walkway Over the Hudson State Historic Park and Berean Park Beach showcase the area's natural beauty. During your stay, check out sights such as Franny Reese State Park, Franklin D Roosevelt Library & Museum, and Apple Greens Golf Course.

When is the best time to book a hotel with a pool in Highland?

Taking into account the local weather in Highland can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Highland are January, February, March, and April, with each month seeing an average of 7 inches of snowfall.

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