Title: The Best Hotels with a Pool in Callicoon from $99 in 2026 | Expedia.com [Callicoon Travel Guide](https://expedia.com/Callicoon.dx183645)[Hotels in Callicoon](https://expedia.com/Callicoon-Hotels.d183645.Travel-Guide-Hotels)[Vacation Rentals in Callicoon](https://expedia.com/Callicoon-Vacation-Rentals.d183645.Travel-Guide-VacationRentals)[Flights to Callicoon](https://expedia.com/Cheap-Flights-To-Callicoon.d183645.Travel-Guide-Flights)[Car Rentals in Callicoon](https://expedia.com/Car-Rentals-In-Callicoon.d183645.Car-Rental-Guide)[Callicoon Vacation Packages](https://expedia.com/Callicoon.d183645.Destination-Travel-Guides) ![Aerial shot of a hill near Callicoon, in the Catskills area of upstate, New York](https://images.trvl-media.com/place/183645/66dcd65e-a7fa-4b9b-bdfd-a01c7a167c3a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/183645/66dcd65e-a7fa-4b9b-bdfd-a01c7a167c3a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Callicoon Hotels with a Pool Tonight [Mar 3 - Mar 4](https://www.expedia.com/Hotel-Search?regionId=183645&startDate=2026-03-03&endDate=2026-03-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 4 - Mar 5](https://www.expedia.com/Hotel-Search?regionId=183645&startDate=2026-03-04&endDate=2026-03-05&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=183645&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=183645&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Callicoon hotels with a pool ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/7e509efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/d481be85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/982ee667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, piano bar](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/6a342d06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Roma Resort and Conference Center [](https://www.expedia.com/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) Callicoon 6.6/10 (397 reviews) "School trip. Got my own room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristel $127 nightly $144 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Indoor pool, open 7 AM to 10 PM, free cabanas, sun loungers](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/95ef3af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Food and drink](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/d6b9765c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Resort view](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/0479130a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bars/lounges](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/90312aff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino [](https://www.expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) Monticello 8.8/10 Excellent (1,079 reviews) "Yessss the hotel was great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelvin $194 nightly $216 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/3b40d2ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/aa91067c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/5214096c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Accessible (Hearing) | In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/b1559701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Monticello [](https://www.expedia.com/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.Hotel-Information) Monticello 9.4/10 Exceptional (639 reviews) "Good continental breakfast, comfortable beds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven $141 nightly $160 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/cd3eed20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/399979ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/291aac28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Monticello [](https://www.expedia.com/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) Monticello 8.2/10 Very Good (1,001 reviews) "Friendly staff and clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin $87 nightly $99 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/21472002.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds | Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/08ed7537.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/b24c479e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/a901755b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Liberty [](https://www.expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) Liberty 6.8/10 (1,001 reviews) "Rooms were clean and ready for occupancy " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas $93 nightly $105 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/1bc406d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![7 bars/lounges](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/6aaba293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/bd1fd61c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Alder at Resorts World Catskills [](https://www.expedia.com/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) Monticello 8.2/10 Very Good (211 reviews) "GREAT SPOT" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rolan $153 nightly $172 total Apr 2 - Apr 3 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Water park](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/7b139e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w966h620x25y37-6819803f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/89050c13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/e6e1e949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Kartrite Resort & Indoor Waterpark [](https://www.expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) Monticello 8.2/10 Very Good (1,996 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Merlyn $288 nightly $326 total Mar 8 - Mar 9 Total with taxes and fees [](https://www.expedia.com/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/110000000/109890000/109882600/109882536/w922h610x4y0-2f924217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/110000000/109890000/109882600/109882536/w926h605x0y5-d6136410.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/110000000/109890000/109882600/109882536/3b459f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/110000000/109890000/109882600/109882536/df2ae630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Arnold House [](https://www.expedia.com/Livingston-Manor-Hotels-The-Arnold-House.h109882536.Hotel-Information) Livingston Manor 8.0/10 Very Good (2 reviews) "Good meal, nice common room, but the hotel is totally overpriced. Our room was small, modestly appointed and had a view of the dumpster. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David $233 nightly $264 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Livingston-Manor-Hotels-The-Arnold-House.h109882536.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/307e38ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/afa28a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Books](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/1bce59ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/9e61c77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Equestrian House Suites [](https://www.expedia.com/Pleasant-Mount-Hotels-Equestrian-House-Suites.h108065055.Hotel-Information) Pleasant Mount $538 nightly $587 total Mar 11 - Mar 12 Total with taxes and fees [](https://www.expedia.com/Pleasant-Mount-Hotels-Equestrian-House-Suites.h108065055.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/612fa592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/13fc1dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/6eb1cb3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/88000000/87740000/87733200/87733136/84a56e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 4 bedroom house with a private pool in a quiet area [](https://www.expedia.com/Glen-Spey-Hotels-Spacious-4-Bedroom-House-With-A-Private-Pool-In-A-Quiet-Area.h87733136.Hotel-Information) Glen Spey 10/10 Exceptional (7 reviews) "Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Johnny A. $392 nightly $441 total Mar 4 - Mar 5 Total with taxes and fees [](https://www.expedia.com/Glen-Spey-Hotels-Spacious-4-Bedroom-House-With-A-Private-Pool-In-A-Quiet-Area.h87733136.Hotel-Information) 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. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-17&endDate=2026-03-18®ionId=183645&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Callicoon Breakfast included 4 stars Hot tub 5 stars Spa ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=AFFINITY_SPRING_PROMO_183645) ## Top Callicoon Hotel Reviews ![Best Western Monticello](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/91f35d31_y.jpg) ### Best Western Monticello 10/10 Excellent "Great room. A little dated overall great. " [](https://expedia.com/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Villa Roma Resort and Conference Center](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/68962920_y.jpg) ### Villa Roma Resort and Conference Center 10/10 Excellent "School trip. Got my own room " [](https://expedia.com/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Days Inn by Wyndham Liberty](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/0d18a8bd_y.jpg) ### Days Inn by Wyndham Liberty 10/10 Excellent "Rooms were clean and ready for occupancy " [](https://expedia.com/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Callicoon with outdoor pools? > 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? ### Which Callicoon hotels offer poolside service for food and drinks? > 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? ### How can I save on a Callicoon hotel with a pool with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Rv Parks in Hankins ](https://www.expedia.com/Hankins-RV-Parks.d553248635975870699-aaRVParks.Travel-Guide-Accommodation) - [Cochecton Hotels ](https://www.expedia.com/Cochecton-Hotels.d6023609.Travel-Guide-Hotels) - [Cabin Rentals in Cochecton ](https://www.expedia.com/Cochecton-Cabins.d6023609-aaCabins.Travel-Guide-Accommodation) - [3 Star Hotels in Cochecton ](https://www.expedia.com/3Star-Cochecton-Hotels.s30-0-d6023609.Travel-Guide-Filter-Hotels) - [Resorts in Cochecton ](https://www.expedia.com/Cochecton-Resorts.d6023609-aaResorts.Travel-Guide-Accommodation) - 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