Title: Book the Best Hotels with POOL in Callicoon in 2025 | Expedia.ca [Hotels in Callicoon](https://expedia.ca/Callicoon-Hotels.d183645.Travel-Guide-Hotels)[Vacation Rentals in Callicoon](https://expedia.ca/Callicoon-Vacation-Rentals.d183645.Travel-Guide-VacationRentals)[Callicoon Car Rentals](https://expedia.ca/Car-Rentals-In-Callicoon.d183645.Car-Rental-Guide)[Callicoon Vacation Packages](https://expedia.ca/Callicoon.d183645.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/e7add73607f5463058c1edbb750cc5cb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Matthew Jay # Find Hotels with a Pool in Callicoon, NY from CA $147 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](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 [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2025-10-08&endDate=2025-10-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2025-10-09&endDate=2025-10-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Callicoon Hotels with a Pool ![Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/2e43c618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hotel Deluxe Room](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/748a3511.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/902000/901998/68962920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Roma Resort and Conference Center Callicoon 6.6/10 (376) "Nice for family gatherings bar server was great." CA $270 CA $305 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/a57b1b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/2696141a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/1bb15d19.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) ### The Alder at Resorts World Catskills Monticello 8.2/10 Very good (181) "Great place to stay " CA $147 CA $202 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/5718c6e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/bf76b331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/e60bb869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/20000/19400/19381/2147b970.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Liberty Liberty 6.8/10 (1006) "Great place to stay, very quiet and clean, the staff was friendly and the breakfast station was more than outstanding " CA $130 CA $147 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ![Waterslide](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d.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) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/w963h620x26y37-b83c1234.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) ### The Kartrite Resort & Indoor Waterpark Monticello 8.2/10 Very good (1745) "Great for quick fam vacay" [](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.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) ![Cabin (Cabin 4 bedroom) | Private kitchen](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/8a861535.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin (Cabin 4 bedroom) | Private kitchen](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/5ae5ca1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/4394a9c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Equestrian House Suites Pleasant Mount CA $157 CA $446 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Pleasant-Mount-Hotels-Equestrian-House-Suites.h108065055.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/66000000/65980000/65976400/65976354/1763e34c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/66000000/65980000/65976400/65976354/8a31e774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/66000000/65980000/65976400/65976354/16673047.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65980000/65976400/65976354/247704d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 minutes from original Woodstock site. Mongaup Valley 9.8/10 Exceptional (58) "What a wonderful house, everything was clean and comfortable. Very convenient to Bethel Woods! The host was friendly and helpful. We would definitely stay here again. " CA $97 CA $258 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Mongaup-Valley-Hotels-5-Minutes-From-Original-Woodstock-Site.h65976354.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/4070f19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/41b49dd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Monticello Monticello 9.4/10 Exceptional (596) "It’s a great place to stay in Montecello" CA $210 CA $237 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.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) ![Property grounds](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49.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) ![Concierge desk](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/e3c7f442.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Resorts World Catskills Casino Monticello 8.6/10 Excellent (1079) "Great place to stay" [](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.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) ![Suite, 1 King Bed, Non Smoking, Kitchenette (Living Room;with Sofabed)](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/2c9f1032.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) ### Best Western Monticello Monticello 8.0/10 Very good (1002) "Our go to spot when in Monticello NY.the staff was wonderful, Breakfast was terrific " CA $158 CA $179 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/115000000/114900000/114895700/114895692/3351ce41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/115000000/114900000/114895700/114895692/f13485cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/115000000/114900000/114895700/114895692/4da2a7c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Courtyard View](https://images.trvl-media.com/lodging/115000000/114900000/114895700/114895692/bec0d8c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Lake Joseph Forestburgh 8.0/10 Very good (8) "Wonderful staff,comfortable stay,excellent variety at breakfast " CA $364 CA $412 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Forestburgh-Hotels-Inn-At-Lake-Joseph.h114895692.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.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23®ionId=183645&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Callicoon Hotel Reviews ![Days Inn by Wyndham Liberty](//images.trvl-media.com/lodging/1000000/20000/19400/19381/e60bb869_y.jpg) ### Days Inn by Wyndham Liberty 10/10 Excellent "Place was quiet, clean and safe" [](https://expedia.ca/Monticello-Hotels-Days-Inn-By-Wyndham-Liberty.h19381.Hotel-Information) ![Villa Roma Resort and Conference Center](//images.trvl-media.com/lodging/1000000/910000/902000/901998/2e43c618_y.jpg) ### Villa Roma Resort and Conference Center 10/10 Excellent "The stay at the resort was very enjoyable. If you book through Orbitz, please call the property and make sure they got your reservation. They had not received ours, but fortunately had a room for us. The room was very large and clean. The whole resort needs a general make-over, as the facility is a bit dated and used (wallpapers, paints, windows, door locks, showers, etc.), but you can see that this hotel still has a lot of prestige. The breakfast buffet was excellent, with an omelette station, eggs, bacon etc. and very friendly and helpful waiters in the restaurant. Happy with our one-night stay. We would come back, should we go back to this area! " [](https://expedia.ca/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information) ![Best Western Monticello](//images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68_y.jpg) ### Best Western Monticello 10/10 Excellent "Location was convenient. Restaurants within walking distance. Breakfast was good and the sauna was a nice bonus. " [](https://expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Callicoon? > [Villa Roma Resort and Conference Center](https://www.expedia.ca/Monticello-Hotels-Villa-Roma-Resort-And-Conference-Center.h901998.Hotel-Information): Features a children's pool, a seasonal outdoor pool, and 3 restaurants. [The Kartrite Resort & Indoor Waterpark](https://www.expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information): Hotel, 7-minute walk from Resorts World Catskills. Offers a children's pool, an indoor pool, and a water park. [Resorts World Catskills Casino](https://www.expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information): Hotel, 4-minute walk from Resorts World Catskills. Provides 6 restaurants, a pool, and a full-service spa. [The Alder at Resorts World Catskills](https://www.expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information): Hotel, 4-minute walk from Resorts World Catskills. Features 7 restaurants, an indoor pool, and a full-service spa. [Callicoon Hills](https://www.expedia.ca/Callicoon-Center-Hotels-Callicoon-Hills.h63163026.Hotel-Information): Offers daily, a pool, and free self parking. ### What is there to see and do in Callicoon? > The picturesque setting of Upper Delaware River and Big Island showcase the area's natural beauty. Discover sights such as Villa Roma Driving Range during your stay. ### When is the best time to book a hotel with a pool in Callicoon? > Taking into account the local weather in Callicoon can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. 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