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Find Hotels with a Pool in Callicoon, NY

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Check prices for these dates, December 15 – 16, 2026

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Our top choices for Callicoon hotels with a pool

1. Villa Roma Resort and Conference Center

A swimming pool with people enjoying the water, surrounded by trees and a stone waterfall feature.

2. Callicoon Hills

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.

3. Days Inn by Wyndham Liberty/Monticello

A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.

4. Best Western Monticello

A large indoor swimming pool with a wooden deck and lounge chairs.

5. Hampton Inn Monticello

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

6. The Kartrite Resort & Indoor Waterpark

An indoor water park with a large slide, seating areas, and a covered central area.

7. Resorts World Catskills Casino

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

8. The Alder at Resorts World Catskills

An indoor swimming pool with clear lanes, a sunlit ceiling, and a view of the outside.

9. The Bradstan Boutique Hotel

A rectangular outdoor swimming pool with a metal ladder, surrounded by greenery and trees.

10. The Arnold House

A cozy indoor seating area with wooden beams, string lights, and potted plants.

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Choose what matters most at hotels with a pool in Callicoon

Breakfast included

4 stars

Hot tub

5 stars

Spa

Top Callicoon Hotel Reviews

The Bradstan Boutique Hotel

A rectangular outdoor swimming pool with a metal ladder, surrounded by greenery and trees.

Hampton Inn Monticello

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

Callicoon Hills

A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.

Resorts World Catskills Casino

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

Best Western Monticello

A large indoor swimming pool with a wooden deck and lounge chairs.

The Kartrite Resort & Indoor Waterpark

An indoor water park with a large slide, seating areas, and a covered central area.

The Alder at Resorts World Catskills

An indoor swimming pool with clear lanes, a sunlit ceiling, and a view of the outside.

The Arnold House

A cozy indoor seating area with wooden beams, string lights, and potted plants.

Frequently Asked Questions

What are the best hotels in Callicoon with outdoor pools?

The Villa Roma Resort and Conference Center is a charming 3-star hotel in Callicoon that features a delightful outdoor pool, great for families looking to unwind after a day of adventure. Guests appreciate the poolside bar, where you can sip refreshing drinks while enjoying the sun on comfortable loungers.

This resort is not just about relaxation; it also offers an array of activities that cater to the adventurous spirit. For those who enjoy winter sports, the Villa Roma has onsite skiing options, including ski lessons and rentals, with nearby ski areas to explore. Reviews highlight the friendly and helpful staff, who contribute to a pleasant atmosphere, as well as the beautifully maintained lobby and bar area, making it an inviting choice for families seeking both fun and comfort.

How much does a hotel with outdoor pool in Callicoon cost?

Enjoy staying in a hotel in Callicoon with an outdoor pool. You can find a great deal from $108 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.

Which Callicoon hotels offer poolside service for food and drinks?

The Villa Roma Resort and Conference Center is a delightful 3-star retreat in Callicoon, superb for families seeking relaxation and fun. This resort features a vibrant poolside bar where guests can enjoy refreshing drinks and delicious snacks without having to leave their sun loungers. The ambiance is lively, and many travellers appreciate the friendly and helpful staff who enhance the overall experience.

In addition to the inviting poolside service, Villa Roma offers a range of amenities that cater to both relaxation and adventure. Families can take advantage of the resort-inclusive atmosphere, which allows for a seamless experience while enjoying the beautiful surroundings. With options for skiing nearby and lessons available on-site, it's an ideal spot for both winter sports enthusiasts and those simply looking to unwind by the pool.

Is it cheaper to book flights and a Callicoon hotel with a pool as a package?

Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it’s wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.

Can I cancel my hotel reservation on Expedia?

Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Callicoon for you.

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