Find Hotels with a Pool in Montgomery, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 Montgomery Hotels with a Pool

Tonight
Nov 28 - Nov 29
Tomorrow
Nov 29 - Nov 30
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Montgomery Hotels with a Pool

Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
  • Outdoor pool
8.6 out of 10, Excellent, (29)
Pool toys transform the outdoor pool into a delightful aquatic playground at this LEGOLAND hotel. After swimming, families can enjoy the on-site restaurant, arcade room, and garden, making this vibrant getaway perfect for creating lasting memories.
The price is ₩194,854
₩407,878 total
includes taxes & fees
Dec 21 - Dec 22
LEGOLAND Hotel NEW York
Indoor pool
Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 star property
Crown Heights
  • Indoor pool
8.8 out of 10, Excellent, (1010)
Splash into the inviting pool that delights families with its clean, warm waters and abundance of fresh towels. Beyond aquatic fun, guests appreciate the well-equipped fitness center, complimentary breakfast buffet, and spacious, comfortable rooms throughout this peaceful retreat.
The price is ₩145,075
₩168,468 total
includes taxes & fees
Dec 6 - Dec 7
Hampton Inn & Suites Poughkeepsie
Indoor pool, sun loungers
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 star property
Chester
  • Indoor pool
  • Pool loungers
8.6 out of 10, Excellent, (1009)
Splash into vacation mode at the pristine indoor pool, complete with inviting sun loungers for post-swim relaxation. Families appreciate the hotel's proximity to LEGOLAND New York while enjoying spotlessly clean rooms with premium bedding and thoughtful amenities.
The price is ₩114,656
₩135,439 total
includes taxes & fees
Nov 30 - Dec 1
Holiday Inn Express Hotel & Suites Chester by IHG
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
  • Indoor pool
8.6 out of 10, Excellent, (1008)
Swimmers enjoy year-round aquatic bliss at the temperature-controlled indoor pool, a perfect complement to the comprehensive 24-hour fitness center. Adventure seekers appreciate nearby hiking trails, while business travelers value the laptop-friendly workspaces.
The price is ₩134,568
₩152,232 total
includes taxes & fees
Dec 8 - Dec 9
Hilton Garden Inn Fishkill
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
  • Full-service spa
8.4 out of 10, Very Good, (1020)
Seasonal outdoor swimming invites summer splashes amid breathtaking mountain scenery. After hiking local trails, guests rejuvenate with spa treatments, including deep-tissue massages and facials, before enjoying fresh cuisine at the onsite café.
The price is ₩174,032
₩196,875 total
includes taxes & fees
Dec 14 - Dec 15
Overlook Lodge at Bear Mountain
Indoor pool
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
Crown Heights
  • Indoor pool
9.0 out of 10, Wonderful, (1015)
Swimmers glide through crystal-clear waters in the immaculately maintained indoor pool, perfect for all-season enjoyment. Modern rooms with sound-insulated walls and thoughtful amenities complement the 24-hour fitness center and inviting firepit area.
The price is ₩147,927
₩171,780 total
includes taxes & fees
Dec 1 - Dec 2
Hyatt Place Poughkeepsie / Hudson Valley
Indoor pool
Homewood Suites by Hilton Poughkeepsie

Homewood Suites by Hilton Poughkeepsie

3.0 star property
Poughkeepsie
  • Indoor pool
9.6 out of 10, Exceptional, (1007)
Swimming enthusiasts relish the pristine indoor pool, accessible from early morning until late evening. After invigorating laps, families gather around the outdoor fire pit, while others enjoy a round of mini golf before retreating to sound-insulated, spacious rooms.
The price is ₩174,324
₩202,434 total
includes taxes & fees
Dec 5 - Dec 6
Homewood Suites by Hilton Poughkeepsie
Indoor pool
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3.0 star property
Poughkeepsie
  • Indoor pool
9.4 out of 10, Exceptional, (382)
Swimming sessions await at the inviting indoor pool, complemented by well-equipped kitchenettes in each spacious room. After a peaceful night's rest, guests savor a delicious breakfast buffet before exploring nearby Vassar College.
The price is ₩158,559
₩184,126 total
includes taxes & fees
Dec 7 - Dec 8
Home2 Suites By Hilton Poughkeepsie
Indoor pool
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 star property
New Paltz
  • Indoor pool
9.4 out of 10, Exceptional, (1008)
Splash into serenity at the immaculate indoor pool after exploring Mohonk Preserve's hiking trails. Fresh breakfast delights await each morning, while spotlessly clean rooms provide peaceful sanctuaries for rejuvenation in this well-maintained retreat.
The price is ₩162,624
₩182,148 total
includes taxes & fees
Dec 22 - Dec 23
Hampton Inn by Hilton New Paltz
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Montgomery Hotel Reviews

Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Loved it. Room was great. Shower and bathroom were large and nice. Nice snacks in the lobby and breakfast spread was great. Highly recommend this hotel."
Kristopher 1-night trip
Posted 3 days ago
Hampton Inn by Hilton New Paltz
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

10/10 Excellent
"Very friendly front desk staff!"
Robert 2-night trip
Posted 5 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Montgomery?
Super 8 by Wyndham Montgomery Maybrook: Hotel, 7-minute walk from Resorts World Catskills. Features a children's pool, an indoor pool, and a water park. Holiday Inn Express & Suites Montgomery by IHG: Offers a snack bar/deli, an indoor pool, and buffet. Borland House Inn: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Features daily, an indoor pool, and complimentary wired internet access. The Kartrite Resort & Indoor Waterpark: Hotel, 1-minute walk from Bear Mountain State Park. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Hampton Inn & Suites Poughkeepsie: Hotel, 4-minute walk from Resorts World Catskills. Provides 6 restaurants, a pool, and a full-service spa.
What is there to see and do in Montgomery?
The picturesque setting of Orange County Arboretum showcases the area's natural beauty. During your stay, check out sights such as City Winery Hudson Valley, Highland Lakes State Park, and Orange County Tennis Center. 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.