Title: The Best Hotels with a Pool in Ossining from $110 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 16 - Feb 17](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-16&endDate=2026-02-17&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 17 - Feb 18](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-17&endDate=2026-02-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 20 - Feb 22](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-20&endDate=2026-02-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining hotels with a pool ![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) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/0ca0a1f1.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. $943 nightly $971 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![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/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa | 5 bedrooms](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/b0adc70f.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 $809 nightly $901 total Mar 16 - Mar 17 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.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) ![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) ![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) ### Heidi's Inn [](https://www.expedia.com/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) Brewster 8.8/10 Excellent (822 reviews) "Clean room with very friendly and helpfull staff with a light breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher $129 nightly $140 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.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) ![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) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/020e6ad2.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 (324 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne $127 nightly $146 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.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) ![Reception](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.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) ### 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 (1,004 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 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/320bd4a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/be0aeba4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, towels, soap, toilet paper](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/2a0deaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/a4d2d147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1-bedroom apartment in Carmel with WiFi, AC [](https://www.expedia.com/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.Hotel-Information) Carmel Hamlet 9.0/10 Wonderful (2 reviews) "Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emmett $257 nightly $279 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.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) ![Dinner served](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/85553e7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/850000/848400/848360/eb2e5670.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) ### Ethan Allen Hotel [](https://www.expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) Danbury 7.8/10 Good (1,139 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 26 - Feb 27 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/8848142c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/15b760e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/3987b0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner and brunch served, Asian cuisine](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/03994778.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tarrytown House Estate [](https://www.expedia.com/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) Tarrytown 8.2/10 Very Good (1,003 reviews) "It was a perfect short stay there" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carl $148 nightly $169 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/40a70d08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/9631af0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/903ceccc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1,059 reviews) "Easy check in, clean room, very good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $106 nightly $130 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/210000/202500/202411/5572c1bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/202500/202411/a3d8eb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/210000/202500/202411/d8313ca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/210000/202500/202411/41204bc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Marriott Danbury [](https://www.expedia.com/Danbury-Hotels-Residence-Inn-Marriott-Danbury.h202411.Hotel-Information) Danbury 8.2/10 Very Good (357 reviews) "Clean room, good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mariela $125 nightly $144 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Residence-Inn-Marriott-Danbury.h202411.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=2026-03-02&endDate=2026-03-03®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 ![](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_6190653) ## Top Ossining Hotel Reviews ![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 "It was simple nothing to complain about but nothing special" [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Westchester Marriott](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/w3995h2667x0y0-3f6e8d0f_y.jpg) ### Westchester Marriott 10/10 Excellent " Room was excellent service in the restaurant was very good front desk hospitality very good .had eonerful stay at the westchester marriott.i will return" [](https://expedia.com/Tarrytown-Hotels-Westchester-Marriott.h10829.Hotel-Information) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 10/10 Excellent "great staff!" [](https://expedia.com/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.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 "Lovely space and kind staff. Breakfast was delicious." [](https://expedia.com/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![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 "Clean nice staff enjoyed the room" [](https://expedia.com/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information) ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Nice big clean room, staff was friendly and kind. Good parking and only a short distance from where I had to go." [](https://expedia.com/Stamford-Hotels-Amsterdam-Hotel.h20793.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 "." [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers-Westchester.h15730982.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Everything was clean and the staff was friendly and helpful " [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Hotel NoMa, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/0bfe077b_y.jpg) ### Hotel NoMa, Trademark Collection by Wyndham 10/10 Excellent "Easy and fast check in good room service Clean white bed sheets " [](https://expedia.com/White-Plains-Hotels-Radisson-Hotel-New-Rochelle.h1088006.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 - 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