TOP Hotels with Swimming Pool in Cragsmoor, NY for 2026

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Cragsmoor Hotels with Swimming Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Cragsmoor hotels with a pool

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.

1. 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.

₹10,328

₹12,200 total

includes taxes & fees

8 Nov - 9 Nov

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 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.

2. 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.

₹11,147

₹13,168 total

includes taxes & fees

8 Nov - 9 Nov

A spacious hotel lobby with a high ceiling, wooden beams, a large mural, and a seating area with a sofa and chairs.

A living room with a sectional sofa, a wooden coffee table, a dining table with chairs, and a wall clock.

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.

3. Harvest Inn

Pine Bush

Seasonal outdoor pool creates an idyllic summer retreat near nature's breathtaking trails.

₹17,122

₹19,370 total

includes taxes & fees

2 Nov - 3 Nov

An indoor swimming pool area with chairs and a sign that reads 'POOLSIDE IS MY VIBE'.

A hotel room with a kitchenette, including a microwave, coffee maker, and sink.

A black electric vehicle charging station with cables connected to it, set against a wooden fence and greenery.

A modern restaurant with a central island, multiple tables, and chairs.

4. Home2 Suites by Hilton Middletown

Middletown

Year-round pool perfection at this hotel, where aquatic bliss awaits after a day of adventure.

₹11,643

₹14,084 total

includes taxes & fees

5 Nov - 6 Nov

An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.

A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.

A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.

A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

5. Hampton Inn Monticello

Monticello

Splash into indoor pool comfort at this Hampton Inn with fitness centre and free breakfast buffet.

₹11,643

₹13,157 total

includes taxes & fees

15 Nov - 16 Nov

A poolside area with red umbrellas, a pool, and a fenced patio with chairs and tables.

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.

A spacious hotel lobby with wooden beams, a central bar area, and seating arrangements.

6. Hampton Inn by Hilton Middletown

Middletown

Seasonal outdoor pool escape awaits at this Middletown hotel, where recreational amenities and adventure opportunities abound.

₹7,585

₹8,959 total

includes taxes & fees

19 Nov - 20 Nov

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 landscaped outdoor area with a fire feature, seating, and a pathway.

A modern hotel lobby with a fireplace, comfortable seating, and a television.

7. Courtyard by Marriott Middletown Goshen

Middletown

Refresh with a splash in this modern hotel's year-round indoor pool near Orange County attractions.

₹9,556

₹11,287 total

includes taxes & fees

9 Nov - 10 Nov

An indoor swimming pool with clear water, surrounded by grey tiled flooring and walls, large windows offering views of the outside, and a lifeguard station with a ladder.

An outdoor patio with a dining table and chairs, a barbecue grill, and a fire pit.

A spacious living area with a stone wall, a flat-screen TV, comfortable seating, and a modern chandelier.

A modern bar area with a stone accent wall, a long wooden bar counter, and a flat-screen TV mounted above the bar.

8. Residence Inn by Marriott Middletown Goshen

Middletown

Take a dip in the modern indoor pool at this Goshen hotel, offering year-round swimming in a spotlessly clean aquatic retreat.

₹17,760

₹20,979 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

Choose what matters most at hotels with a pool in Cragsmoor

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Cragsmoor Hotel Reviews

Best Western Monticello

8/10 Good

"Very nice hotel"

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

10/10 Excellent

"The arrival was easy and three lady was awesome! Great customer service"

Fairfield Inn & Suites by Marriott Goshen Middletown

8/10 Good

"King suite a little strange, because tv is very far from bed. Have to turn up volume very loud and hard to see for older people. No electricity on one side of bed for charging devices on night table. Also, lots of road noise from highway on front side of building."

Ramada by Wyndham Newburgh/West Point

8/10 Good

"Was under construction, room was clean and comfortable."

Courtyard by Marriott Middletown Goshen

10/10 Excellent

"Room was very clean 👌 wonderful staff highly recommended!!! Will be staying there again in the future. Pool & whirlpool A++"

Howard Johnson by Wyndham Newburgh/West Point

10/10 Excellent

"Good stay"

Frequently asked questions

What are some hotels with pools in Cragsmoor?

The Kartrite Resort & Indoor Waterpark: Hotel located near Resorts World Catskills. Offers a children's pool, an indoor pool and a water park. Sleep Inn & Suites Middletown - Goshen: Provides continental, an indoor pool and complimentary high-speed (wired) Internet access. Resorts World Catskills Casino: Hotel, 4-minute walk from Resorts World Catskills. Features 6 restaurants, a pool and a full-service spa. La Quinta Inn & Suites by Wyndham Middletown-Goshen: Offers buffet, an indoor pool and free self parking. Ramada by Wyndham Newburgh/West Point: Offers free self parking, an indoor pool and complimentary wireless Internet access.

What is there to see and do in Cragsmoor?

Spend some time experiencing the great outdoors at Minnewaska State Park and VerKeerderkill Falls. Discover sights such as Ellenville Fault Ice Caves during your stay.

When is the best time to book a hotel with a pool in Cragsmoor?

Taking the local weather in Cragsmoor into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Cragsmoor are January, February, March and April, with each month seeing an average of 16 cm of snowfall.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Swimming Pool in Cragsmoor on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Cragsmoor Hotels with Swimming Pool

Our top choices for Cragsmoor hotels with a pool

1. La Quinta Inn & Suites by Wyndham Middletown-Goshen