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
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Montgomery hotels with a pool

A swimming pool with a wooden deck, lounge chairs, and a red umbrella.
A wooden cabin with a covered deck, outdoor seating, and a fire pit.
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.

1. Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
$187 nightly
$221 total
Nov 3 - Nov 4
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
A pool area with a hot tub, a pool lift, and safety signs on the walls.
A hotel room with two beds, a desk, a TV, and a chair.
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.

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.
$107 nightly
$127 total
Nov 10 - Nov 11
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A pool area with lounge chairs and a hot tub.
A landscaped outdoor area with a fire feature, seating, and a pathway.
A modern hotel lobby with a seating area, large windows, and a television screen.
A modern hotel lobby with a fireplace, comfortable seating, and a television.

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
Nov 8 - Nov 9
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 spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A Hampton Inn hotel with a modern design, featuring a covered entrance and a well-lit facade.
A gym with exercise equipment, treadmills, and weight machines.

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.
$80 nightly
$94 total
Nov 19 - Nov 20
Total with taxes and fees
Hampton Inn by Hilton Middletown
An indoor pool area with a covered roof, multiple seating arrangements, and a view of the outside.
A hotel room with a large bed, bedside lamps, a desk, a chair, and a television.
A gym with stationary bikes, a treadmill, and exercise balls.
A Red Roof Inn & Suites building with a two-story structure, a balcony, and an American flag.

5. 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 25 - Oct 26
Total with taxes and fees
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
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.

6. Harvest Inn

Harvest Inn
Pine Bush
  • Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.
$179 nightly
$203 total
Oct 30 - Oct 31
Total with taxes and fees
Harvest Inn
A Hampton Inn & Suites by Hilton hotel with a large illuminated sign, modern architecture, and a well-lit facade.
A store interior with shelves stocked with various snacks and treats, a chalkboard with a message, and a wall with a circular design.
A hotel room with two beds, a nightstand with a lamp, a phone, and a clock.
A modern bathroom with a walk-in shower, grab bars, and a white towel hanging on the wall.

7. 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.
$135 nightly
$160 total
Nov 22 - Nov 23
Total with taxes and fees
Hampton Inn & Suites Newburgh Stewart Airport
An indoor swimming pool with a lifeguard chair, poolside chairs, and a clear view of the outside through large windows.
A modern hotel with a two-story structure, a covered entrance, and a parking lot with marked spaces.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.
A modern breakfast area with a blue wall, wooden cabinets, and a tiled floor.

8. 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.
$118 nightly
$139 total
Oct 26 - Oct 27
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 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.
A modern living room with a large TV, comfortable seating, and a patterned rug.

9. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
$116 nightly
$137 total
Oct 27 - Oct 28
Total with taxes and fees
Candlewood Suites Middletown Goshen by IHG
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 conference room with a desk, two monitors, a chair, and a blue sofa.

10. 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.
$152 nightly
$180 total
Nov 1 - Nov 2
Total with taxes and fees
Homewood Suites Stewart Airport
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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
"Excellent place—nice room and fine breakfast"
Norman 1-night trip
Posted 17 hours ago
Holiday Inn Express Poughkeepsie by IHG
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Was under construction, room was clean and comfortable."
Gary 4-night trip
Posted 2 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: 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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