Title: The Best Ossining Hotels with Pools from $106 - Hotels with indoor pools in Ossining, NY | 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 [Mar 9 - Mar 10](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-09&endDate=2026-03-10&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 10 - Mar 11](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-10&endDate=2026-03-11&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-20&endDate=2026-03-22&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) ![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) ![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/f958fa55.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) "Super fun location! Host was very helpful. The house is very comfortable for large groups " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) natalie l. $924 nightly $950 total Mar 19 - Mar 20 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/b0adc70f.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) ### NEW 45 Wolden Rd Ossining NY 10562 [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining $952 nightly $1,060 total Mar 15 - Mar 16 Total with taxes and fees [](https://www.expedia.com/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.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) ![Banquet hall](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/8626bd92.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) ![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 (1,003 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 $102 nightly $116 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.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 (823 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 Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.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 8.0/10 Very Good (1,168 reviews) "Clean room | Staff | Breakfast | Business-friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eimy $92 nightly $106 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Ethan-Allen-Hotel.h848360.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) ![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) ![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) ### 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 (331 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne $127 nightly $146 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.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) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110790000/110784600/110784547/c06f2598.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 Mar 10 - Mar 11 Total with taxes and fees [](https://www.expedia.com/Carmel-Hotels-Charming-1-Bedroom-Apartment-In-Carmel-With-WiFi.h110784547.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) ![One King Bed Studio | Living area | 55-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/7a9acd26.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 (1,070 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 Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/c39ed8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 11:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/97c64d65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/9a2b47a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/30000/26800/26788/0d5d6da0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel MTK Mount Kisco [](https://www.expedia.com/White-Plains-Hotels-Holiday-Inn-Mt-Kisco.h26788.Hotel-Information) Mount Kisco 8.6/10 Excellent (1,005 reviews) "Great hotel. The town is nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric $139 nightly $159 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/White-Plains-Hotels-Holiday-Inn-Mt-Kisco.h26788.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/22000000/21830000/21829200/21829133/e8acd4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21830000/21829200/21829133/1c4aba7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/22000000/21830000/21829200/21829133/494195c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21830000/21829200/21829133/ca7ff701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Paramus [](https://www.expedia.com/Paramus-Hotels-Hampton-Inn-Paramus.h21829133.Hotel-Information) Paramus 9.2/10 Wonderful (1,002 reviews) "Staff was courteous and helpful, room was very clean, bed comfortable, and excellent breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George Ann $107 nightly $123 total Mar 22 - Mar 23 Total with taxes and fees [](https://www.expedia.com/Paramus-Hotels-Hampton-Inn-Paramus.h21829133.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=2026-03-23&endDate=2026-03-24®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 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_6190653) ## Top Ossining Hotel Reviews ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "Very friendly staff. Quick and easy check in. Clean room. " [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/76900125_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "pool was very relaxing and heated was a nice touch. Bar was amazing " [](https://expedia.com/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.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 "Yes " [](https://expedia.com/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/2db42e29_y.jpg) ### Hampton Inn & Suites Yonkers 10/10 Excellent "Excellent room space and cleanliness " [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](https://images.trvl-media.com/lodging/1000000/30000/23300/23291/ea472a69_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Perfect location right off Highway and inly 45 minutes to JFK. Friendly staff, decent breakfast and the coffee and cookies hit the spot when we arrived! Room was clean and perfect for our one night stay. Would absolutely stay there again. " [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/b7afffa4_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Front desk was very accommodating. I requested a room with a view of the Hudson and he looked until he found one. Room was clean and spacious. I would use this property again" [](https://expedia.com/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Hyatt Place New York/Yonkers](https://images.trvl-media.com/lodging/11000000/10240000/10232200/10232108/w3837h2558x3y3-5267f15f_y.jpg) ### Hyatt Place New York/Yonkers 10/10 Excellent "Very clean room, friendly staff " [](https://expedia.com/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information) ![Armoni Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 2/10 Terrible "The pictures do no justice to the absolute disgusting appeal this place brings. The staff wasn’t helpful at all. The hotel itself had a feint marijuana smell the whole time. Our sheets were dirty with marks on it. The room wasn’t vacuumed. Exposed wiring and unusable lamps. Soda machine completely opened. Back door completely unlocked no key card necessary to enter so security is terrible. Was given a soap bar the size of my left pinky toe to wash my grown man body with. Booked the room for two adults and two children but my room only had two towels available. The carpet seemed like it was coming up and it was extremely stained. Overall my experience was unsatisfactory." [](https://expedia.com/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 6/10 Okay "Not great" [](https://expedia.com/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.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 - Flights - Packages - Cars - Vacation Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [Hotels near Sing Sing Prison Museum ](https://www.expedia.com/Sing-Sing-Prison-Museum-Hotels.0-l553248621561873062-0.Travel-Guide-Filter-Hotels) - [Hotels near Snowden Avenue Park ](https://www.expedia.com/Snowden-Avenue-Park-Hotels.0-l553248621558038861-0.Travel-Guide-Filter-Hotels) - 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