Find Hotels with a Pool in Montgomery, NY

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Check availability on Montgomery Hotels with a Pool

Our top choices for Montgomery hotels with a pool

Exterior
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

Montgomery
10.0 out of 10, Exceptional, (2)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is AED 583
AED 909 total
includes taxes & fees
4 Jan - 5 January 2026
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
BBQ/picnic area
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Room was clean and staff was great!"
United States
Annemarie
The price is AED 276
AED 326 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn by Hilton Middletown
Outdoor pool
LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York

3.0 star property
Goshen
8.8 out of 10, Excellent, (33)
"We are having a great time at the hotel!!!"
United States
Ziwei
The price is AED 699
AED 1,272 total
includes taxes & fees
22 Dec - 23 Dec
LEGOLAND Hotel NEW York
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
8.6 out of 10, Excellent, (1001)
"The staff was excellent "
United States
Kelley
The price is AED 382
AED 451 total
includes taxes & fees
12 Dec - 13 Dec
Holiday Inn Express Hotel & Suites Chester by IHG
Seasonal outdoor pool
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 star property
Bear Mountain
8.4 out of 10, Very Good, (1005)
"Staff was incredibly kind and the room was super cozy. The inn is beautiful and there is enough to do around. "
United States
Ryan
The price is AED 393
AED 445 total
includes taxes & fees
30 Dec - 31 Dec
Overlook Lodge at Bear Mountain
Indoor pool
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3.0 star property
Crown Heights
9.0 out of 10, Wonderful, (1008)
"Lovely property, wonderful staff will definitely return back."
United States
Dennis
The price is AED 371
AED 431 total
includes taxes & fees
15 Dec - 16 Dec
Hyatt Place Poughkeepsie / Hudson Valley
Sports facility
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

3.0 star property
Fishkill
8.6 out of 10, Excellent, (1005)
"Brayden was great"
United States
Will
The price is AED 337
AED 381 total
includes taxes & fees
4 Jan - 5 January 2026
Hilton Garden Inn Fishkill
Indoor pool
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

2.5 star property
New Paltz
9.4 out of 10, Exceptional, (1000)
"The hotel is quiet and clean and had a very comfortable bed."
United States
Carolyn
The price is AED 408
AED 457 total
includes taxes & fees
21 Dec - 22 Dec
Hampton Inn by Hilton New Paltz
Indoor pool
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3.0 star property
Middletown
9.4 out of 10, Exceptional, (934)
"great staff, clean rooms, nice breakfast .. overall a pleasant & safe atmosphere !"
United States
Emerson
The price is AED 428
AED 505 total
includes taxes & fees
4 Jan - 5 January 2026
La Quinta Inn & Suites by Wyndham Middletown-Goshen
Indoor pool
Home2 Suites By Hilton Poughkeepsie

Home2 Suites By Hilton Poughkeepsie

3.0 star property
Poughkeepsie
9.4 out of 10, Exceptional, (390)
"Beautiful room and great staff! Would stay here again. "
United States
Christina
The price is AED 398
AED 462 total
includes taxes & fees
24 Dec - 25 Dec
Home2 Suites By Hilton Poughkeepsie
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.
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Top Montgomery Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"He was excellent our two nights and thank again, see you soon."
Abdou karime 2-night trip
Posted 3 days ago
Hampton Inn Harriman Woodbury

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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 daily, an indoor pool, and free self parking. Borland House Inn: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. The Kartrite Resort & Indoor Waterpark: Offers a snack bar/deli, an indoor pool, and buffet. Quality Inn Poughkeepsie: Hotel, 1-minute walk from Woodbury Common Premium Outlets. Provides daily, an indoor pool, and complimentary wired internet access.
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.