Title: The Best Hotels with a Pool in Ossining from $94 in 2026 | Expedia.com [Ossining Travel Guide](https://expedia.com/Ossining.dx6190653)[Hotels in Ossining](https://expedia.com/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Vacation Rentals in Ossining](https://expedia.com/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.com/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Car Rentals in Ossining](https://expedia.com/Car-Rentals-In-Ossining.d6190653.Car-Rental-Guide)[Ossining Vacation Packages](https://expedia.com/Ossining.d6190653.Destination-Travel-Guides) ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by louann ohora ![](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.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 Ossining Hotels with a Pool Tonight [Feb 5 - Feb 6](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-05&endDate=2026-02-06&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 6 - Feb 7](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-06&endDate=2026-02-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-13&endDate=2026-02-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining hotels with a pool ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/11e211e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW 45 Wolden Rd Ossining NY 10562 [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining $836 nightly $932 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/f6243b7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/f958fa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/6407ae3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! [](https://www.expedia.com/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) Ossining 9.2/10 Wonderful (7 reviews) "Communication was excellent. The house itself is older and fine for its age, but " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan O. $880 nightly $904 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![Indoor pool, open 8:30 AM to 9:30 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/800/736/df09fa9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/800/736/b3a2ed01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3832h2559x4y0-2bb2a540.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Nanuet [](https://www.expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) Nanuet 9.0/10 Wonderful (1,062 reviews) "Clean room, helpful staff and good bar/restaurant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephen $102 nightly $118 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/383ffb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/13890846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/7384700a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very Good (1,000 reviews) "The stone lodges are cute and cozy and the staff were quick and helpful if you needed anything. Great for a short stay at a reasonable price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Judith $104 nightly $118 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/353de5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/b84054b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/bb9d6c7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/85553e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ethan Allen Hotel [](https://www.expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) Danbury 7.8/10 Good (1,131 reviews) "Clean room | Staff | Breakfast | Business-friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eimy $95 nightly $110 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/8c8893e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/af6569cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/e52257ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1560000/1551400/1551336/354c26b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Nanuet [](https://www.expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) Nanuet 7.8/10 Good (1,000 reviews) "very helpful and nice staff, room was spacious and clean. good price and had breakfast included. will come back !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Riachelle $81 nightly $94 total Mar 1 - Mar 2 Total with taxes and fees [](https://www.expedia.com/Nyack-Hotels-Hampton-Inn-Nanuet.h1551336.Hotel-Information) ![Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/58f7f74c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/501c20f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/b27e2d2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Nyack, a JdV by Hyatt Hotel [](https://www.expedia.com/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) Nyack 8.6/10 Excellent (1,002 reviews) "I loved the hotel and its decor and ambience. I would definitely recommend the hotel and I will be staying there again !!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen $147 nightly $168 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/57d22171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed | Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/ff2ecf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/cc0a2b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/b0b0d087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG [](https://www.expedia.com/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) Danbury 9.2/10 Wonderful (321 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne $127 nightly $146 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/8808b113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/2561a581.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/0bfe077b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/6edcc77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel NoMa, Trademark Collection by Wyndham [](https://www.expedia.com/White-Plains-Hotels-Radisson-Hotel-New-Rochelle.h1088006.Hotel-Information) Downtown Rochelle 8.2/10 Very Good (1,004 reviews) "Excellent hotel will definitely use it again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick $123 nightly $141 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/White-Plains-Hotels-Radisson-Hotel-New-Rochelle.h1088006.Hotel-Information) ![Land view from property](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/407ec306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/cf8502df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/03b916e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/a57d093b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heidi's Inn [](https://www.expedia.com/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) Brewster 8.8/10 Excellent (820 reviews) "Big , clean , updated room and very friendly and helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael $129 nightly $140 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.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=2026-02-19&endDate=2026-02-20®ionId=6190653&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Ossining Breakfast included Hot tub 4 stars 5 stars Ocean view ## Top Ossining Hotel Reviews ![Hyatt Place New York/Yonkers](https://images.trvl-media.com/lodging/11000000/10240000/10232200/10232108/w3837h2558x3y3-6fc198b6_y.jpg) ### Hyatt Place New York/Yonkers 10/10 Excellent "Very clean, quiet" [](https://expedia.com/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Thank you to the staff at DoubleTree in Nanuet, NY. Excellent service Clean rooms Respectful staff Great breakfast. Thank you again… 😊" [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Amazing courteous and professional staff very good p" [](https://expedia.com/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Hotel Nyack, a JdV by Hyatt Hotel](https://images.trvl-media.com/lodging/12000000/11950000/11943100/11943081/a38df02c_y.jpg) ### Hotel Nyack, a JdV by Hyatt Hotel 10/10 Excellent "Very quiet and the staff stayed out of my way as I wanted. Beautiful property and the price was exceptional. Will make this my go to whenever I am in the Hudson Valley. " [](https://expedia.com/Nyack-Hotels-Hotel-Nyack.h11943081.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "Room was very clean and comfortable. " [](https://expedia.com/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![Hampton Inn & Suites Yonkers - Westchester](https://images.trvl-media.com/lodging/16000000/15740000/15731000/15730982/2770772f_y.jpg) ### Hampton Inn & Suites Yonkers - Westchester 10/10 Excellent "Clean Rooms, Great Staff, Indoor pool, gym, free parking and delicious breakfast." [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers-Westchester.h15730982.Hotel-Information) ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Room was very clean upon arrival. Staff was very friendly. " [](https://expedia.com/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "clean, usb-c socket, very friendly staff, free shuttle to airport..," [](https://expedia.com/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg) ### Hampton Inn & Suites Yonkers 10/10 Excellent "Staff was kind and helpful" [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Ossining? ### What is there to see and do in Ossining? ### When is the best time to book a hotel with a pool in Ossining? ### What's the best way to travel around Ossining? ## Explore a world of travel with Expedia - Lodging - 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