The Best Hotels with a Pool in Highland, NY from ￥19,577 in 2026

Q: What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie : Offers a snack bar/deli, an indoor pool, and free self parking. Hyatt Place Poughkeepsie / Hudson Valley : Provides a full-service spa, a seasonal outdoor pool, and 3 bars. Beekman Arms and Delamater Inn : Hotel, 7-minute walk from Vassar College. Features daily, an indoor pool, and free self parking. DoubleTree by Hilton Poughkeepsie Convention Center : Offers a snack bar/deli, an indoor pool, and buffet. Holiday Inn Express Poughkeepsie by IHG : Features free self parking, an indoor pool, and complimentary wireless internet access.

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Our top choices for Highland hotels with a pool

1. Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

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

￥25,580 total

includes taxes & fees

Aug 19 - Aug 20

2. Hampton Inn & Suites Poughkeepsie

Crown Heights

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

￥22,163 total

includes taxes & fees

Aug 11 - Aug 12

3. 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.

￥19,577 total

includes taxes & fees

Aug 9 - Aug 10

4. Homewood Suites by Hilton Poughkeepsie

Poughkeepsie

Relax at the warm, inviting indoor pool with year-round access for water-filled fun at this Poughkeepsie retreat.

￥26,829 total

includes taxes & fees

Aug 18 - Aug 19

5. Residence Inn by Marriott Poughkeepsie

Poughkeepsie

Inviting indoor pool and hot tub for all-season relaxation at this comfortable hotel near Vassar College and Locust Grove.

￥26,136 total

includes taxes & fees

Aug 30 - Aug 31

6. SpringHill Suites by Marriott Fishkill

Fishkill

Soak up relaxation at this family-friendly hotel with a pristine indoor pool for year-round swims.

￥30,758 total

includes taxes & fees

Aug 30 - Aug 31

7. HYATT house Fishkill/Poughkeepsie

Fishkill

Sleek indoor pool sanctuary with bubbling hot tub invites relaxation, complete with plush loungers for ultimate comfort.

￥22,588 total

includes taxes & fees

Aug 16 - Aug 17

8. Best Western Fishkill Inn & Suites

Fishkill

Seasonal outdoor pool for summer dips makes this hotel a perfect family-friendly getaway.

￥25,652 total

includes taxes & fees

Aug 9 - Aug 10

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Choose what matters most at hotels with a pool in Highland

Breakfast included

Hot tub

Top Highland Hotel Reviews

Americas Best Value Inn New Paltz

10/10 Excellent

"Clean and very covenient"

Quality Inn Poughkeepsie

8/10 Good

"Staff, room and parking were great. Breakfast was very disappointing. Space is part of the problem and the coffee maker wasn't working, so staff was having to refill a thermo container. Food choices were very limited mainly due to the space. Its also not practical to have the single desk staff also dealing with the breakfast. Again,room and staff were great. I didn't use the pool or other amenities"

Frequently asked questions

What are some accommodations with pools in Highland?

SureStay Plus Hotel by Best Western Highland Poughkeepsie: Offers a snack bar/deli, an indoor pool, and free self parking. Hyatt Place Poughkeepsie / Hudson Valley: Provides a full-service spa, a seasonal outdoor pool, and 3 bars. Beekman Arms and Delamater Inn: Hotel, 7-minute walk from Vassar College. Features daily, an indoor pool, and free self parking. DoubleTree by Hilton Poughkeepsie Convention Center: Offers a snack bar/deli, an indoor pool, and buffet. Holiday Inn Express Poughkeepsie by IHG: Features free self parking, an indoor pool, and complimentary wireless 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 Franklin D Roosevelt Library & Museum, Apple Greens Golf Course, and Franny Reese State Park.

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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