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Find Hotels with a Pool in Montgomery, NY

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Check availability on Montgomery Hotels with a Pool

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Montgomery hotels with a pool

A swimming pool with a wooden deck, lounge chairs, and a red umbrella.
A small wooden cabin with a deck, outdoor seating, and a view of a lake.
A bathroom with a toilet, a shower, and a wooden floor.
A wooden cabin with a covered deck, outdoor seating, and a fire pit.

1. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
$207 nightly
$245 total
Oct 6 - Oct 7
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a seating area with tables.
A modern bathroom with a large mirror, a sink, and a shower.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
A modern hotel with a prominent 'La Quinta' sign, large windows, and a covered entrance area.

2. La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen
Middletown
  • Immerse in a serene aquatic escape at this family-friendly hotel featuring a pristine indoor pool and relaxation hot tub.
$120 nightly
$141 total
Nov 2 - Nov 3
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A swimming pool with chairs and sun loungers, large windows, and a tiled wall with a wavy pattern.
A modern bar area with a curved counter, bar stools, and a television screen.
A modern hotel lobby with a seating area, large windows, and a television screen.
A landscaped outdoor area with a fire feature, seating, and a pathway.

3. Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen
Middletown
  • Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.
$101 nightly
$119 total
Oct 28 - Oct 29
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
A pool area with clear signage, including a 'NO DIVING' sign, and a 'SPA RULES' notice.
A hotel lobby with a seating area, a bar, and a view of the city.
A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.
A modern hotel room with a flat-screen TV, a desk with drawers, a comfortable sofa, a bed, and a large window with curtains.

4. Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport
Newburgh
  • Splash into comfort at this airport hotel's indoor oasis with plush loungers and spa-like relaxation.
$144 nightly
$170 total
Oct 4 - Oct 5
Total with taxes and fees
Courtyard by Marriott Newburgh Stewart Airport
A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.
A living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a wall clock.
An outdoor patio area with tables and chairs, colorful umbrellas, and a building with stone and concrete exterior.
A neatly made bed with white bedding and a pillow with the text "Be Our Guest." There are two bedside lamps on wooden nightstands, one on each side of the bed.

5. Harvest Inn

Harvest Inn
Pine Bush
  • Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.
$164 nightly
$185 total
Oct 26 - Oct 27
Total with taxes and fees
Harvest Inn
A hotel lobby with a reception desk, bar area, and a television displaying news.
A hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.
A hotel room with a bed, desk, TV, and a sofa.
A Hampton Inn & Suites hotel with a modern facade, large windows, and a well-lit entrance.

6. Hampton Inn & Suites Newburgh Stewart Airport

Hampton Inn & Suites Newburgh Stewart Airport
Newburgh
  • Splash into year-round relaxation at this hotel's indoor swimming oasis, just minutes from Algonquin Park and local attractions.
$139 nightly
$164 total
Oct 28 - Oct 29
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
An indoor pool area with a covered roof, multiple seating arrangements, and a view of the outside.
A hotel lobby with a reception desk, a sofa, a staircase, and a patterned carpet.
A hotel lobby with a sofa, two patterned armchairs, a coffee table, a wall-mounted sign, a staircase, and a patterned carpet.
A bathroom with a white sink, a mirror, a hairdryer, and a shower curtain.

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

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.
$99 nightly
$117 total
Oct 18 - Oct 19
Total with taxes and fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

8. Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
Middletown
  • Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.
$89 nightly
$106 total
Nov 2 - Nov 3
Total with taxes and fees
Hampton Inn by Hilton Middletown
A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.
A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.
A spacious living area with a curved sofa, a fireplace, and a modern chandelier.
A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.

9. Homewood Suites Stewart Airport

Homewood Suites Stewart Airport
New Windsor
  • Dive into blissful relaxation at this hotel's indoor pool oasis with bubbling hot tub escape.
$147 nightly
$174 total
Nov 1 - Nov 2
Total with taxes and fees
Homewood Suites Stewart Airport
An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A modern restaurant with a central island, multiple tables, and chairs.

10. Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
Middletown
  • Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.
$155 nightly
$187 total
Nov 1 - Nov 2
Total with taxes and fees
Home2 Suites by Hilton Middletown
View all properties

Choose what matters most at hotels with a pool in Montgomery

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Montgomery Hotel Reviews

Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"Good hotel for the price, breakfast very good"
Mark 1-night trip
Posted 5 hours ago
Sleep Inn & Suites Middletown - Goshen
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Have stayed few times. It is our pick. Clean, great location."
THERESA 1-night trip
Posted 9 hours ago
Hampton Inn by Hilton New Paltz
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Friendly staff, quick check in, easy parking. Room was clean and comfortable. Easy access to Bear Mountain. Nice restaurant. No elevator in Overlook Lodge so a few trips required to bring luggage upstairs."
Mary 1-night trip
Posted 3 days ago
Overlook Lodge at Bear Mountain
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

8/10 Good
"Overall good stay staff was good rooms were clean. Will stay again"
Thomas 3-night trip
Posted 3 days ago
Holiday Inn Express & Suites Montgomery by IHG

Frequently asked questions

What are some accommodations with pools in Montgomery?
Holiday Inn Express & Suites Montgomery by IHG: Hotel located near Resorts World Catskills. Provides a children's pool, an indoor pool, and a water park. Super 8 by Wyndham Montgomery Maybrook: Hotel, 7-minute walk from Vassar College. Features daily, an indoor pool, and free self parking. 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. Quality Inn Poughkeepsie: Features continental, an indoor pool, and complimentary wired internet access. Overlook Lodge at Bear Mountain: Hotel, 4-minute walk from Resorts World Catskills. Offers 6 restaurants, a pool, and a full-service spa.
What is there to see and do in Montgomery?
Explore places like Woodbury Common Premium Outlets while you're in the area. The picturesque setting of Thomas Bull Memorial Park and Orange County Arboretum 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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