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

Find Hotels with a Pool in Montgomery, NY from CA $149

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Check availability on Montgomery Hotels with a Pool

Tonight
Sep 28 - Sep 29
Tomorrow
Sep 29 - Sep 30
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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
CA $174
CA $344 total
includes taxes & fees
Oct 6 - Oct 7
Historic Cabin with Pool & Fire Pit
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 Courtyard Marriott hotel with a covered entrance, outdoor seating area, and multiple balconies.
A modern living room with a sectional sofa, two armchairs, a coffee table, and a TV.

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.
CA $190
CA $224 total
includes taxes & fees
Oct 4 - Oct 5
Courtyard by Marriott Newburgh Stewart Airport
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 bar area with a curved counter, bar stools, 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.
CA $149
CA $176 total
includes taxes & fees
Oct 12 - Oct 13
Courtyard by Marriott Middletown Goshen
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 bathroom with a large mirror, a sink, and a shower.
A hotel room with two beds, a desk, a TV, and a chair.

4. 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.
CA $190
CA $224 total
includes taxes & fees
Sep 29 - Sep 30
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 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.

5. 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.
CA $145
CA $171 total
includes taxes & fees
Oct 6 - Oct 7
Hampton Inn 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.
An outdoor patio area with tables and chairs, colorful umbrellas, and a building with stone and concrete exterior.
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.
CA $232
CA $263 total
includes taxes & fees
Oct 7 - Oct 8
Harvest Inn
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 hotel reception desk with a large 'happy.' poster on the wall, a counter with a computer, and a display of brochures.
A Hampton Inn & Suites hotel with a modern facade, large windows, and a well-lit entrance.

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.
CA $196
CA $231 total
includes taxes & fees
Oct 28 - Oct 29
Hampton Inn & Suites Newburgh Stewart Airport
An indoor swimming pool with a sunroof, a pool table, and a seating area with chairs.
A stainless steel refrigerator with a water dispenser, located in a hallway with a tiled floor and a door on the left.
A hotel room with a large bed, two bedside tables, a desk, a chair, a flat-screen TV, and a wardrobe.
A hotel lobby with a sofa, chairs, a coffee table, a desk, and a chandelier.

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.
CA $126
CA $149 total
includes taxes & fees
Oct 18 - Oct 19
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
An indoor swimming pool with a 9-foot depth warning.
A hotel with a central entrance pavilion, a flag, and a landscaped garden.
A hotel room with a bed, a sofa, a TV, a desk, and a wall with a geometric pattern.
A Simon Premium Outlet sign at Woodbury Commons.

9. 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.
CA $168
CA $207 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express Hotel & Suites Chester by IHG
A rectangular swimming pool with a metal ladder, surrounded by a low fence and trees.
An outdoor patio with round tables and chairs, covered by large umbrellas, and a pergola structure.
A spacious lobby with a stone accent wall, a flat-screen TV, and a seating area with sofas and a coffee table.
A modern living room with a stone accent wall, a flat-screen TV, and a fireplace. There are multiple seating options including a sofa, chairs, and a table.

10. Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
Goshen
  • Seasonal outdoor pool offers refreshing dips during warm summer months in Goshen.
CA $168
CA $207 total
includes taxes & fees
Oct 26 - Oct 27
Fairfield Inn & Suites by Marriott Goshen Middletown
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

10/10 Excellent
"Was a pleasant overnight stay"
david 1-night trip
Posted 19 hours ago
Ramada by Wyndham Newburgh/West Point
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

10/10 Excellent
"Everything was excellent. No complains"
Maria 1-night trip
Posted 23 hours ago
Sleep Inn & Suites Middletown - Goshen
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

8/10 Good
"Beautiful and relaxing. Something I’d do different next time, I’d definitely stay at the Inn. As a solo female traveler, the Overlook was too secluded - it broke some of the solo traveling rules I’ve set for myself. Also, was a little bummed the next morning. Upon check in I was told about their Fall Foliage Buffet. I opted to do this instead of brunch the next day. Turns out that morning was a Princess Brunch, which canceled out the buffet and I had shown up after brunch hours. But the cafe was open and I was able to get a little something there."
Lindsay 1-night trip
Posted 1 day ago
Overlook Lodge at Bear Mountain
Holiday Inn Express & Suites Montgomery by IHG

Holiday Inn Express & Suites Montgomery by IHG

10/10 Excellent
"Everything was great. Next visit I will get a handicapped room. With a walk in shower."
phyllis 2-night trip
Posted 3 days 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: 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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