TOP Hotels with Pool in Montgomery, NY for 2026

Q: What are some accommodation options with pools in Montgomery?

Super 8 by Wyndham Montgomery Maybrook : Hotel steps from The Kartrite Resort & Indoor Waterpark. Provides a children's pool, an indoor pool and a water park. Holiday Inn Express & Suites Montgomery by IHG : Features a snack bar/deli, an indoor pool and free self parking. The Kartrite Resort & Indoor Waterpark : Hotel, 4-minute walk from Resorts World Catskills. Features 6 restaurants, a pool and a full-service spa. Hyatt Place Poughkeepsie / Hudson Valley : Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Spark by Hilton Fishkill : Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli.

Two large silos, a barn, and a green field under a blue sky.

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Our top choices for Montgomery hotels with a pool

The Kartrite Resort & Indoor Waterpark

Monticello

Splash into four-season aquatic fun at this family paradise with both indoor and outdoor pool playgrounds.

฿10,757 total

includes taxes & fees

12 Jul - 13 Jul

Indoor pool, open 7 AM to 10 PM, free pool cabanas, pool loungers

Resorts World Catskills Casino

Monticello

Indoor pool paradise with casino thrills, spa indulgences, and mountain adventure awaits at this luxury hotel.

฿9,231 total

includes taxes & fees

23 Jul - 24 Jul

Seasonal outdoor pool, pool umbrellas, pool loungers

LEGOLAND Hotel NEW York

Goshen

Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.

฿15,847 total

includes taxes & fees

15 Jul - 16 Jul

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.

฿4,999 total

includes taxes & fees

26 Jul - 27 Jul

Home2 Suites By Hilton Poughkeepsie

Poughkeepsie

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

฿5,989 total

includes taxes & fees

14 Jul - 15 Jul

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.

฿4,985 total

includes taxes & fees

12 Jul - 13 Jul

Home2 Suites by Hilton Middletown

Middletown

Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.

฿7,651 total

includes taxes & fees

20 Jul - 21 Jul

Fairfield Inn & Suites by Marriott Goshen Middletown

Goshen

Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.

฿5,900 total

includes taxes & fees

19 Jul - 20 Jul

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Choose what matters most at hotels with a pool in Montgomery

Breakfast included

Hot tub

Top Montgomery Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

8/10 Good

"We took our grandchildren to Legoland and chose this hotel for its proximity to the park, indoor pool and breakfast features. Well, it was 20 minutes away, which wasn’t as close as I thought. I thought I had read it was 9 minutes away but it must have been 9 miles, which took 20+ minutes. My mistake, I’m sure. The indoor pool was heavily chlorinated. It was also occupied our entire time there (approximately 1.5 hours) with children taking swimming lessons. Our grandchildren were still able to swim but needed to stay at one end of the pool and be overly mindful of the little ones as they came swimming into “our side” of the pool. Again, no big deal but not ideal. Breakfast was fine-the kids really enjoyed making their own waffles. As far as the hotel goes, it was okay-dated but clean. The staff was friendly and helpful. There is no restaurant on premise but we were given a sheet with names of nearby restaurants. None were in walking distance so we chose to order in and had pizza (and beer!) delivered. Overall, our stay was fine-not great but it worked for us."

Frequently asked questions

What are some accommodation options with pools in Montgomery?

Super 8 by Wyndham Montgomery Maybrook: Hotel steps from The Kartrite Resort & Indoor Waterpark. Provides a children's pool, an indoor pool and a water park. Holiday Inn Express & Suites Montgomery by IHG: Features a snack bar/deli, an indoor pool and free self parking. The Kartrite Resort & Indoor Waterpark: Hotel, 4-minute walk from Resorts World Catskills. Features 6 restaurants, a pool and a full-service spa. Hyatt Place Poughkeepsie / Hudson Valley: Offers continental, an indoor pool and complimentary high-speed (wired) Internet access. Spark by Hilton Fishkill: Hotel, 1-minute walk from Bear Mountain State Park. Provides a full-service spa, a seasonal outdoor pool and a snack bar/deli.

What is there to see and do in Montgomery?

Explore places such as LEGOLAND® New York and Woodbury Common Premium Outlets while you're in the area. The picturesque setting of Orange County Arboretum and Thomas Bull Memorial Park showcase the area's natural beauty. You'll also discover lots of options for restaurants in Montgomery.

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

Taking the local weather in Montgomery into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Montgomery are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

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