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 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
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 bathroom with a toilet, a shower, and a wooden floor.
A wooden ladder in a room with a patterned rug, wooden cabinets, and a view of a red barn through a door.
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
$193 nightly
$228 total
Nov 3 - Nov 4
Total with taxes and fees
Historic Cabin with Pool & Fire Pit
An indoor swimming pool with clear water, surrounded by walls with a blue and white color scheme, and equipped with safety railings and seating areas.
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.
$108 nightly
$128 total
Nov 15 - Nov 16
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Middletown-Goshen
A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.
A modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.
A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.
A gym with exercise equipment, treadmills, and weight machines.

3. 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 18 - Nov 19
Total with taxes and fees
Hampton Inn by Hilton Middletown
A pool area with lounge chairs and a hot tub.
A modern hotel lobby with a seating area, large windows, and a television screen.
A modern bar area with a curved counter, bar stools, and a television screen.
A landscaped outdoor area with a fire feature, seating, and a pathway.

4. 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 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Middletown Goshen
An indoor swimming pool with a sunroof, a pool table, and a seating area with chairs.
A bathroom with a white sink, a mirror, a telephone, and a shower curtain.
A hotel lobby with a reception desk, two staircases, and a carpeted floor.
A hotel lobby with a sofa, two patterned armchairs, a coffee table, a wall-mounted sign, a staircase, and a patterned carpet.

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.
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.
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.
$184 nightly
$208 total
Oct 26 - Oct 27
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 bar area with a long counter, multiple bar stools, and a variety of bottles.
A gym with treadmills, elliptical machines, and a large window with a view of buildings.
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.
$144 nightly
$170 total
Oct 28 - Oct 29
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 breakfast area with a blue wall, wooden cabinets, and a tiled floor.
A modern reception area with a wooden desk, two chairs, a colorful striped artwork on the wall, and a patterned carpet.
A hotel room with two beds, a nightstand with a phone, and a wall-mounted light fixture.

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 25 - Oct 26
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 hotel sign for Candlewood Suites, an IHG hotel, with a parking lot and cars in front.
A modern kitchen area with a coffee machine, a refrigerator stocked with beverages, and a coffee station with various coffee products.

9. Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG
Middletown
$110 nightly
$130 total
Oct 26 - Oct 27
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 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.
A multi-story hotel with a prominent entrance, stone pillars, and a well-maintained lawn.

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
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

Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

8/10 Good
"Fine basic motel. Lots of parking, easy access to highway, lots of places to eat nearby. Bed was very comfortable."
Justin Robert 2-night trip
Posted 1 hour ago
Ramada by Wyndham Newburgh/West Point
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

8/10 Good
"Great stay"
Justine 1-night trip
Posted 2 hours ago
Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

10/10 Excellent
"Bear Mountain Inn is a unique and beautiful retreat in the heart of the Hudson Valley. We go for the scenery, hiking, and watching the marine and rail traffic along the Hudson River. Staff is always helpful. We booked 2 nights but could only. stay 1 due to a family emergency and the staff worked with Expedia to refund the 2nd night. Will definitely return as we love the atmosphere. Stayed in 1 of the stone cottages in the woods above the lake. Basic room with a shared common area and outdoor porch/deck. Room had a small refrigerator and TV with local channels. Clean and quiet and what you'd expect in a state or national park setting. Great 1.5 mile paved walking trail below the cottage that circles the picturesque lake on the property grounds. Nice way to start the day."
Robert K 2-night trip
Posted 2 days ago
Overlook Lodge at Bear Mountain
Hampton Inn by Hilton New Paltz

Hampton Inn by Hilton New Paltz

10/10 Excellent
"Great as always!!"
Susan 1-night trip
Posted 3 days ago
Hampton Inn by Hilton New Paltz

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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