A rural landscape with a house surrounded by autumn-colored trees and rolling hills.

Find Hotels with a Pool in Callicoon, NY

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Check availability on Callicoon Hotels with a Pool

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Callicoon hotels with a pool

A water park with a water play structure and people enjoying the water.
A hotel lobby with round tables, cushioned chairs, a large pillar, and a projection screen displaying a movie.
A wooden building with a staircase leading to a balcony, surrounded by snow and trees.
A hotel reception area with a wooden reception desk, multiple computer monitors, and a large chandelier.

1. Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center
Callicoon
  • Year-round aquatic adventures await at this resort with indoor and seasonal outdoor pools, a waterslide, and poolside bar.
$205 nightly
$231 total
Oct 4 - Oct 5
Total with taxes and fees
Villa Roma Resort and Conference Center
A swimming pool with lounge chairs and umbrellas, surrounded by trees and a building.
A triangular tent-style room with a bed, a small table, and a red lamp.
A large house with multiple sections, including a patio area with outdoor furniture and a stone pathway.
An indoor venue with wooden beams, tables set for dining, and hanging greenery.

2. Callicoon Hills

Callicoon Hills
Callicoon Center
$261 nightly
$295 total
Oct 8 - Oct 9
Total with taxes and fees
Callicoon Hills
A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.
A spacious indoor area with multiple tables and chairs, a kitchen area with a counter, and a large window providing natural light.
A banquet hall with round tables covered in white tablecloths and chairs, a carpeted floor, and a ceiling with recessed lighting.
A hotel room with two beds, a desk, a chair, and a large painting on the wall.

3. Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello
Liberty
  • Dive into poolside serenity at this Liberty hotel, where comfortable loungers invite all-day relaxation beside sparkling waters.
$87 nightly
$98 total
Nov 1 - Nov 2
Total with taxes and fees
Days Inn by Wyndham Liberty/Monticello
An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.
A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.
A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.
A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

4. Hampton Inn Monticello

Hampton Inn Monticello
Monticello
  • Splash into indoor pool comfort at this Hampton Inn with fitness center and free breakfast buffet.
$123 nightly
$139 total
Nov 3 - Nov 4
Total with taxes and fees
Hampton Inn Monticello
A rectangular outdoor swimming pool with a metal ladder, surrounded by greenery and trees.
A lakeside walkway with a wooden deck, surrounded by trees and a building with illuminated windows.
A restaurant with a long dining table, multiple chairs, and a high ceiling with hanging lights.
A modern building with a wooden walkway leading to a covered entrance.

5. The Bradstan Boutique Hotel

The Bradstan Boutique Hotel
Eldred
  • Serene lakeside retreat offers relaxing swims, hot tub soaks, and lounge areas for ultimate outdoor relaxation by the water.
$364 nightly
$411 total
Nov 1 - Nov 2
Total with taxes and fees
The Bradstan Boutique Hotel
An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.
A modern hotel with a prominent glass facade and a distinctive logo on the building.
A modern bar area with a central island, bar stools, and overhead lighting.
An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.

6. Resorts World Catskills Casino

Resorts World Catskills Casino
Monticello
  • Indoor pool paradise with casino thrills, spa indulgences, and mountain adventure awaits at this luxury hotel.
$177 nightly
$197 total
Oct 13 - Oct 14
Total with taxes and fees
Resorts World Catskills Casino
An indoor water park with a large water slide, a pool area, and a glass ceiling structure.
A modern building with a sign reading "The Kartrite Resort & Indoor Waterpark".
A hotel with a pool area, outdoor seating, and a view of the sunset.
A modern apartment complex with a pool, outdoor seating, and a view of the sunset.

7. The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark
Monticello
  • Splash into four-season aquatic fun at this family paradise with both indoor and outdoor pool playgrounds.
$270 nightly
$296 total
Oct 4 - Oct 5
Total with taxes and fees
The Kartrite Resort & Indoor Waterpark
A large indoor swimming pool with a wooden deck and lounge chairs.
A hotel with a brick facade, a covered entrance, and a parking lot with cars.
A reception area with a marble counter, a wall-mounted artwork, and a ceiling with recessed lighting.
A modern living room with two sofas, a glass coffee table, and a painting of a horse.

8. Best Western Monticello

Best Western Monticello
Monticello
  • Dive into refreshing leisure at this hotel's indoor pool sanctuary, complete with sun loungers and a rejuvenating sauna.
$114 nightly
$128 total
Oct 12 - Oct 13
Total with taxes and fees
Best Western Monticello
A poolside area with lounge chairs and striped umbrellas, surrounded by a wooden fence and trees.
A sunroom with wooden beams, large windows, and a variety of potted plants.
A spacious dining area with multiple tables and chairs, large potted plants, and a view of the outdoors through large windows.
A large white house with a green roof, surrounded by a well-maintained lawn and a view of a lake.

9. Kenoza Hall

Kenoza Hall
Kenoza Lake
  • Seasonal outdoor pool sanctuary offers sun-soaked relaxation amid hiking trails at this indulgent spa retreat in the countryside.
$400 nightly
$451 total
Oct 27 - Oct 28
Total with taxes and fees
Kenoza Hall
An indoor swimming pool with a central column, tiled floor, and a skylight above.
An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.
A reception area with a wooden reception desk, a chandelier, and a sign that reads "AWANA SPA & WELLNESS".
An outdoor bar area with a stainless steel counter, bar stools, and a variety of bottles.

10. The Alder at Resorts World Catskills

The Alder at Resorts World Catskills
Monticello
  • Enjoy all-season splashes in the indoor aquatic oasis, where relaxation flows as freely as the water at this Catskills retreat.
$160 nightly
$181 total
Nov 3 - Nov 4
Total with taxes and fees
The Alder at Resorts World Catskills
View all properties

Choose what matters most at hotels with a pool in Callicoon

Breakfast included
4 stars
Hot tub
5 stars
Spa

Top Callicoon Hotel Reviews

Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent
"Restaurant was amazing . Staff very informative about history of Woodstock"
Mary 1-night trip
Posted 17 hours ago
Days Inn by Wyndham Liberty/Monticello

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 $98 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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