Title: Callicoon Vacation Rentals from CA $194: Short-Term Rentals for 2026 | Expedia.ca [Hotels in Callicoon](https://expedia.ca/Callicoon-Hotels.d183645.Travel-Guide-Hotels)[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) ![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__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=183645&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Callicoon vacation rentals ![View from property](https://images.trvl-media.com/lodging/111000000/110500000/110493300/110493257/a291b1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, shampoo](https://images.trvl-media.com/lodging/111000000/110500000/110493300/110493257/268ac142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/111000000/110500000/110493300/110493257/cef80fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 1 Queen Bed | Private kitchen](https://images.trvl-media.com/lodging/111000000/110500000/110493300/110493257/cba31de3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cabin in Roscoe [](https://www.expedia.ca/Postcard-Cabins-Western-Catskills.h110493257.Hotel-Information) 9.4/10 Exceptional (91 reviews) "Great stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CJ CA $122 CA $194 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Postcard-Cabins-Western-Catskills.h110493257.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/9e61c77e.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) ![Dining](https://images.trvl-media.com/lodging/109000000/108070000/108065100/108065055/4894c94a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pleasant Mount [](https://www.expedia.ca/Pleasant-Mount-Hotels-Equestrian-House-Suites.h108065055.Hotel-Information) CA $287 CA $828 total includes taxes & fees Mar 3 - Mar 4 [](https://www.expedia.ca/Pleasant-Mount-Hotels-Equestrian-House-Suites.h108065055.Hotel-Information) ![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/0f6e5d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/859f8d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/5054eba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/121000000/120130000/120124500/120124415/2893d4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aparthotel in Highland Lake [](https://www.expedia.ca/Highland-Lake-Hotels-2-Lake-Cabins-Poolhottub-Game-Room-23acs.h120124415.Hotel-Information) CA $215 CA $1,362 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Highland-Lake-Hotels-2-Lake-Cabins-Poolhottub-Game-Room-23acs.h120124415.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=2026-03-13&endDate=2026-03-14®ionId=183645&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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.ca/deals?rfrr=VR_SPRING_PROMO_183645) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=COTTAGE) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=APARTMENT) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=VILLA) Residences [](https://www.expedia.ca/Hotel-Search?destination=Callicoon%2C+New+York%2C+United+States+of+America®ionId=183645&latLong=41.767311%2C-75.056278&adults=2&startDate=2026-05-28&d1=2026-05-28&endDate=2026-05-31&d2=2026-05-31&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCallicoon-Vacation-Rentals.d183645.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCallicoon-Vacation-Rentals.d183645.Travel-Guide-VacationRentals) ## Top Callicoon Hotel Reviews ![The Kartrite Resort & Indoor Waterpark](https://images.trvl-media.com/lodging/32000000/31690000/31681700/31681637/90ceac4d_y.jpg) ### The Kartrite Resort & Indoor Waterpark 10/10 Excellent "Our room was nice and clean. Overall stay was so much fun. This is our second visit with small children. " [](https://expedia.ca/Monticello-Hotels-The-Kartrite-Resort-Indoor-Waterpark.h31681637.Hotel-Information) ### Postcard Cabins Western Catskills, Outdoor Collection by Marriott Bonvoy 10/10 Excellent "It was such amazing time. Much needed reset. Everything was perfect! Staff were so fast with responses. I just loved everything about it." [](https://expedia.ca/Postcard-Cabins-Western-Catskills.h110493257.Hotel-Information) ![Best Western Monticello](https://images.trvl-media.com/lodging/1000000/30000/26600/26518/68dcbd68_y.jpg) ### Best Western Monticello 10/10 Excellent "Clean rooms, good breakfast, staff was very professional. " [](https://expedia.ca/Monticello-Hotels-Best-Western-Monticello.h26518.Hotel-Information) ![YO1 Longevity & Health Resorts, Catskills](https://images.trvl-media.com/lodging/32000000/31880000/31874000/31873964/ac19baa1_y.jpg) ### YO1 Longevity & Health Resorts, Catskills 10/10 Excellent "Absolutely beautiful and relaxed resort. I was caught off guard, I wasn’t expecting such a nice resort. The room was fantastic!" [](https://expedia.ca/Monticello-Hotels-YO1-Health-Resort.h31873964.Hotel-Information) ![The Bradstan Boutique Hotel](https://images.trvl-media.com/lodging/88000000/87420000/87410200/87410153/a17bcc8b_y.jpg) ### The Bradstan Boutique Hotel 10/10 Excellent "The rooms, the hotel were absolutely gorgeous and clean. The staff was amazing and friendly, extremely kind and helpful. The breakfast was not a continental breakfast, more like a fabulous feast, so much. Lounge is a great place to relax, super spacious. Cant wait to come back in the summer to see the entire grounds " [](https://expedia.ca/Eldred-Hotels-The-Eldred-Preserve.h87410153.Hotel-Information) ![Hampton Inn Monticello](https://images.trvl-media.com/lodging/76000000/75040000/75030700/75030626/41b49dd0_y.jpg) ### Hampton Inn Monticello 10/10 Excellent "Very clean and comfortable 👌 " [](https://expedia.ca/Monticello-Hotels-Hampton-Inn-Monticello.h75030626.Hotel-Information) ![Resorts World Catskills Casino](https://images.trvl-media.com/lodging/24000000/23980000/23970300/23970267/ecb80f49_y.jpg) ### Resorts World Catskills Casino 10/10 Excellent "Excellent clean room friendly staff. Need more roulette tables" [](https://expedia.ca/Monticello-Hotels-Resorts-World-Catskills-Casino.h23970267.Hotel-Information) ![The Alder at Resorts World Catskills](https://images.trvl-media.com/lodging/101000000/101000000/100997000/100996967/9db559da_y.jpg) ### The Alder at Resorts World Catskills 10/10 Excellent "GREAT SPOT" [](https://expedia.ca/Monticello-Hotels-The-Alder-At-Resorts-World-Catskills.h100996967.Hotel-Information) ![Ledges Hotel](https://images.trvl-media.com/lodging/6000000/5330000/5320100/5320032/7e678dea_y.jpg) ### Ledges Hotel 10/10 Excellent "Beautiful setting. The Lounge area and fireplace were perfect for a winter stay. The history of the building gave it an extra layer of interest. The rooms were unique, a nice mix of modern industrial and comfort. The bar and restaurant were fantastic, loved the view of the snowy waterfall. We’d love to return in the warmer weather to enjoy the outdoor decks. " [](https://expedia.ca/Hawley-Hotels-Ledges-Hotel.h5320032.Hotel-Information) ## Find out more about Callicoon You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Callicoon. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Callicoon ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Lodges in Callicoon ](https://expedia.ca/Callicoon-Lodges.d183645-aaLodges.Travel-Guide-Accommodation) - [Inns in Callicoon ](https://expedia.ca/Callicoon-Inns.d183645-aaInns.Travel-Guide-Accommodation) - [Guest Houses in Callicoon ](https://expedia.ca/Callicoon-Guest-Houses.d183645-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in Callicoon ](https://expedia.ca/Callicoon-Motels.d183645-aaMotels.Travel-Guide-Accommodation) - [B&B in Callicoon ](https://expedia.ca/Callicoon-Bed-And-Breakfast.d183645-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Villas in Callicoon ](https://expedia.ca/Callicoon-Villas.d183645-aaVillas.Travel-Guide-Accommodation) - [Country Houses in Callicoon ](https://expedia.ca/Callicoon-Country-House.d183645-aaCountryHouse.Travel-Guide-Accommodation) - [Condo Rentals in Callicoon ](https://expedia.ca/Callicoon-Condos.d183645-aaCondos.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Callicoon? ### What are some of the best vacation home rentals that Callicoon has to offer? ### How many vacation rentals are there in Callicoon? ### What’s there to see and do in Callicoon? ### What’s a vacation rental in Callicoon like? ### Expedia's Latest Trends Hotels - 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