Two large silos, a barn, and a green field under a blue sky.

Find Hotels with a Pool in Montgomery, NY

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Check availability on Montgomery Hotels with a Pool

Tonight
Sep 23 - Sep 24
Tomorrow
Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 wooden cabin with a covered deck, outdoor seating, and a fire pit.
A wooden ladder in a room with a patterned rug, wooden cabinets, and a view of a red barn through a door.

1. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
$189 nightly
$223 total
Sep 29 - Sep 30
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A pool area with clear signage, including a 'NO DIVING' sign, and a 'SPA RULES' notice.
A modern hotel room with a flat-screen TV, a desk with drawers, a comfortable sofa, a bed, and a large window with curtains.
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.

2. 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.
$114 nightly
$135 total
Oct 4 - Oct 5
Total with taxes and fees
Courtyard by Marriott Newburgh Stewart Airport
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 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.
$105 nightly
$125 total
Oct 12 - Oct 13
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
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.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

4. 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.
$102 nightly
$120 total
Oct 6 - Oct 7
Total with taxes and fees
Hampton Inn by Hilton Middletown
A hotel lobby with a reception desk, bar area, and a television displaying news.
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.
A hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.

5. 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.
$152 nightly
$179 total
Oct 4 - Oct 5
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
An indoor swimming pool with a tiled floor, surrounded by lounge chairs and a high, sloped ceiling.
A bathroom with a white sink, a mirror, a hairdryer, and a shower curtain.
A hotel room with a flat-screen TV mounted on a cabinet, a desk with a chair, and a small refrigerator.
A Red Roof Inn & Suites with a two-story building, a balcony, and a flagpole.

6. 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 pool area with a hot tub, a pool lift, and safety signs on the walls.
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.
A modern bathroom with a large mirror, a sink, and a shower.

7. 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.
$134 nightly
$158 total
Sep 27 - Sep 28
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
An indoor swimming pool with a 9-foot depth warning.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A Simon Premium Outlet sign at Woodbury Commons.

8. Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
Chester
  • Refreshing indoor pool sanctuary promises relaxation near LEGOLAND, with loungers for post-adventure unwinding.
$101 nightly
$124 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chester by IHG
An outdoor patio with a grill, chairs, and tables, featuring a red umbrella and string lights.
A compact kitchen with a stainless steel refrigerator, a microwave, and a dishwasher.
A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.
An indoor swimming pool with a tiled edge, surrounded by orange and teal chairs, and large windows allowing natural light.

9. 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
Sep 30 - Oct 1
Total with taxes and fees
Home2 Suites by Hilton Middletown
A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.
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.
A bathroom with a granite countertop sink, a mirror, a towel rack with folded towels, a toilet paper holder, and a trash can.
A living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a wall clock.

10. Harvest Inn

Harvest Inn
Pine Bush
  • Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.
$186 nightly
$210 total
Sep 24 - Sep 25
Total with taxes and fees
Harvest Inn
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

Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

10/10 Excellent
"Nice place, clean, lot of places to eat close by. Will stay here again."
Anthony 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Montgomery by IHG
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

8/10 Good
"food was not great."
Kara 2-night trip
Posted 1 day ago
Hampton Inn by Hilton New Paltz
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

10/10 Excellent
"Very nice staff and very helpful. Clean and spacious rooms."
Ruby 1-night trip
Posted 2 days ago
Holiday Inn Express Poughkeepsie by IHG
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

10/10 Excellent
"Non"
bhaeldin 2-night trip
Posted 11 days ago
Ramada by Wyndham Newburgh/West Point

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: Features daily, an indoor pool, and free self parking. The Kartrite Resort & Indoor Waterpark: Offers continental, an indoor pool, and complimentary wired internet access. Quality Inn Poughkeepsie: Hotel, 1-minute walk from Bear Mountain State Park. Features a full-service spa, a seasonal outdoor pool, and a snack bar/deli. Sleep Inn & Suites Middletown - Goshen: 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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