The Best Hotels with a Pool in Highland, NY from ￥18,565 in 2026

Q: What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie : Offers free self parking, an indoor pool, and complimentary wireless internet access. Best Western Plus Kingston Hotel And Conference Center : Offers a snack bar/deli, an indoor pool, and free self parking. Spark by Hilton Fishkill : Resort located near Mohonk Preserve Visitor Center. Features a full-service spa, a seasonal outdoor pool, and 3 bars. The Crossroads Hotel, Newburgh : Features free self parking, an indoor pool, and complimentary wireless internet access. Hyatt Place Poughkeepsie / Hudson Valley : Offers daily, an indoor pool, and free self parking.

panoramic view of mid hudson bridge over hudson river valley (poughkeepsie, upstate new york) sunny day train station wide angle sun glare crossing suspension small town travel metro north

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Highland Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Highland hotels with a pool

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.

￥18,565 total

includes taxes & fees

Jun 29 - Jun 30

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.

￥19,929 total

includes taxes & fees

Jun 29 - Jun 30

Hampton Inn & Suites Poughkeepsie

Crown Heights

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

￥19,683 total

includes taxes & fees

Jun 29 - Jun 30

Hampton Inn by Hilton New Paltz

New Paltz

Immerse in aquatic serenity at this New Paltz hotel's pristine indoor pool retreat.

￥26,750 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.

￥22,637 total

includes taxes & fees

Jul 13 - Jul 14

Comfort Suites Fishkill near Interstate 84

Fishkill

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

￥19,639 total

includes taxes & fees

Jul 13 - Jul 14

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

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

￥25,898 total

includes taxes & fees

Jul 6 - Jul 7

Courtyard by Marriott Kingston

Kingston

Indoor pool sanctuary offers year-round swimming in a bright, spotless setting just steps from your room.

￥24,946 total

includes taxes & fees

Jun 21 - Jun 22

View all properties

Choose what matters most at hotels with a pool in Highland

Breakfast included

Hot tub

Top Highland Hotel Reviews

Courtyard by Marriott Poughkeepsie

8/10 Good

"Breakfast is not capable."

Quality Inn Poughkeepsie

8/10 Good

"My first non-smoking room smelled very strongly of smoke. (Why do people smoke in non-smoking rooms??) The woman at the front desk was so kind and helpful throughout my stay and moved me to a different room. Second room was okay, a little run down but it was clean enough and the AC worked. There is a waffle maker at breakfast, which is fun, but the rest of the spread is very basic--however, free coffee, so I won't complain! The pool looked nice. The fitness room had a recumbent bike, a treadmill, and an elliptical. The AC was unfortunately broken so the room was HOT but they did set up a fan for me."

Frequently asked questions

What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie: Offers free self parking, an indoor pool, and complimentary wireless internet access. Best Western Plus Kingston Hotel And Conference Center: Offers a snack bar/deli, an indoor pool, and free self parking. Spark by Hilton Fishkill: Resort located near Mohonk Preserve Visitor Center. Features a full-service spa, a seasonal outdoor pool, and 3 bars. The Crossroads Hotel, Newburgh: Features free self parking, an indoor pool, and complimentary wireless internet access. Hyatt Place Poughkeepsie / Hudson Valley: Offers daily, an indoor pool, and free self parking.

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.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Highland on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Highland Hotels with a Pool

Our top choices for Highland hotels with a pool