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

Find Hotels with a Pool in Montgomery, NY

Check availability on Montgomery Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 wooden ladder in a room with a patterned rug, wooden cabinets, and a view of a red barn through a door.
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
$207 nightly
$245 total
Oct 19 - Oct 20
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 modern hotel lobby with a large dining area, comfortable seating, and a flat-screen TV mounted on the wall.
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.
$109 nightly
$129 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 modern hotel lobby with a fireplace, comfortable seating, and a television.
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.

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 1 - Nov 2
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 modern living room with a fireplace, two armchairs, a coffee table, and a TV mounted on the wall.

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.
$84 nightly
$99 total
Nov 9 - Nov 10
Total with taxes and fees
Hampton Inn by Hilton Middletown
An indoor swimming pool with a tiled floor, surrounded by lounge chairs and a high, sloped ceiling.
A hotel room with a sofa, a small table, a TV, a desk with a chair, and a bed.
A hotel room with a desk, two chairs, a printer, and a sign indicating free Wi-Fi in all rooms.
A bathroom with a toilet, sink, and mirror.

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
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 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.

6. 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.
$114 nightly
$135 total
Nov 15 - Nov 16
Total with taxes and fees
Holiday Inn Express & Suites Middletown - Goshen by IHG
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.
An outdoor patio area with tables and chairs, colorful umbrellas, and a building with stone and concrete exterior.
A living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a wall clock.

7. Harvest Inn

Harvest Inn
Pine Bush
  • Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.
$182 nightly
$206 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 reception desk with a large poster on the wall and a person seated behind it.
A store interior with shelves stocked with various snacks and treats, a chalkboard with a message, and a wall with a circular design.
A modern bathroom with a walk-in shower, grab bars, and a white towel hanging on the wall.

8. 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
A hotel indoor pool with lounge chairs, a hot tub, and a warning sign.
A conference room with a desk, two monitors, a chair, and a blue sofa.
A spacious hotel lobby with a large dining table, comfortable seating, and ceiling fans.
A spacious living area with a curved sofa, a fireplace, and a modern chandelier.

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.
$152 nightly
$180 total
Nov 1 - Nov 2
Total with taxes and fees
Homewood Suites Stewart Airport
A swimming pool with colorful umbrellas and lounge chairs.
A hotel room with a large bed, a bookshelf, a mural, and a window with curtains.
A family inside an elevator with a blue patterned floor and a wall with cartoon characters.
A colorful play area with a check-in counter and a mascot.

10. LEGOLAND Hotel NEW York

LEGOLAND Hotel NEW York
Goshen
  • Splash into aquatic adventures at this family retreat with an outdoor pool, playful toys, and refreshing waters.
$188 nightly
$221 total
Oct 18 - Oct 19
Total with taxes and fees
LEGOLAND Hotel NEW York
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 Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

10/10 Excellent
"!"
Sergei 1-night trip
Posted 12 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

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

8/10 Good
"Parking was great"
Kathie Campbell 3-night trip
Posted 2 days ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ 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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