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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 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
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 bathroom with a toilet, a shower, and a wooden floor.
A small wooden cabin with a deck, outdoor seating, and a view of a lake.
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
$206 nightly
$243 total
Nov 3 - Nov 4
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 with a prominent 'La Quinta' sign, large windows, and a covered entrance area.
A modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.

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.
$114 nightly
$135 total
Nov 1 - Nov 2
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 fireplace, comfortable seating, and a television.
A modern hotel lobby with a seating area, large windows, and a television screen.

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 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 kitchenette, a living area with a sofa and a TV, and a large window with curtains.
A Hampton Inn & Suites hotel with a modern facade, large windows, and a well-lit entrance.

4. 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
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 modern living room with a sectional sofa, two armchairs, a coffee table, and a TV.
A Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.

5. 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.
$139 nightly
$165 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Newburgh Stewart Airport
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A gym with exercise equipment, treadmills, and weight machines.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.

6. 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 spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.
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.

7. 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 pool area with a covered roof, multiple seating arrangements, and a view of the outside.
A bathroom with a white sink, a mirror, a hairdryer, and a shower curtain.
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.

8. 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
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

9. Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG
Middletown
  • Make a splash in this hotel's tranquil indoor pool, steps away from LEGOLAND® New York.
$111 nightly
$131 total
Nov 3 - Nov 4
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
A swimming pool with four lounge chairs and a metal ladder.
A modern living room with a large TV, comfortable seating, and a patterned rug.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.
A circular outdoor seating area with a fire pit in the center, surrounded by wicker chairs and a small table.

10. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
$118 nightly
$139 total
Oct 19 - Oct 20
Total with taxes and fees
Candlewood Suites Middletown Goshen by IHG
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Choose what matters most at hotels with a pool in Montgomery

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Montgomery Hotel Reviews

Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"It was quiet and front desk was helpful."
Bernadette 1-night trip
Posted less than an hour ago
Holiday Inn Express Poughkeepsie by IHG
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"I enjoyed the breakfast, especially the waffles. The staff was very nice and accommodating. The only problem was they did not know how to explain how to get back to interstate 17 E. I feel that the staff should be able to give proper directions. Also, there was a lot of construction, and it was hard to turn into the hotel."
Roberta 1-night trip
Posted 5 hours ago
Sleep Inn & Suites Middletown - Goshen
Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

8/10 Good
"Convenient"
Tina 1-night trip
Posted 19 hours ago
Quality Inn Poughkeepsie
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

8/10 Good
"Room was great. All facilities were clean and decor is very nice, modern and not old or worn out. Breakfast was above average. Only big problem was the use of the ev charger. My daughter has an ev and the front desk person was not helpful at all to my daughter in trying to turn in the power for the charger. It took way too many calls, downstairs visits and back and forth questions until front desk staff finally turned it on. Not sure why this was such a problem but it took way too away from everything else that was very good."
patricia m. 1-night trip
Posted 21 hours ago
Hampton Inn by Hilton New Paltz
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

10/10 Excellent
"Very clean and friendly"
Darwin 1-night trip
Posted 1 day 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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