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

Q: What are some accommodations with pools in Montgomery?

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

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Our top choices for Montgomery hotels with a pool

Historic Cabin with Pool & Fire Pit

Montgomery

￥46,595 total

includes taxes & fees

Jun 22 - Jun 23

Sleep Inn & Suites Middletown - Goshen

Middletown

Serene indoor pool sanctuary adds year-round relaxation to your Middletown adventure.

￥25,702 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.

￥25,817 total

includes taxes & fees

Jul 5 - Jul 6

Overlook Lodge at Bear Mountain

Bear Mountain

Majestic seasonal pool beckons with mountain views, perfect for summer relaxation after exploring scenic Bear Mountain trails.

￥29,022 total

includes taxes & fees

Jun 22 - Jun 23

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 30 - Jul 1

Hampton Inn by Hilton Middletown

Middletown

Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.

￥22,165 total

includes taxes & fees

Jul 1 - Jul 2

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.

￥19,938 total

includes taxes & fees

Jun 21 - Jun 22

Holiday Inn Express Hotel & Suites Chester by IHG

Chester

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

￥25,465 total

includes taxes & fees

Jun 17 - Jun 18

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Choose what matters most at hotels with a pool in Montgomery

Breakfast included

Hot tub

Top Montgomery Hotel Reviews

Overlook Lodge at Bear Mountain

10/10 Excellent

"A small room but a great location. Bed was comfortable and A/C worked well. A little noisy, since the rooms are close to each other. Can be a bit of a challenge to find the room we were staying in. The staff was incredibly nice and helpful and the room was clean."

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 Montgomery?

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

What is there to see and do in Montgomery?

Explore places like 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 into account the local weather in Montgomery is an important factor for planning your visit, especially if you plan to spend your trip poolside. 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 Montgomery are January, February, March, and April, with each month seeing an average of 6 inches of snowfall.

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