Title: Book The Best Hotels in Ossining, NY for 2026 from CA $155 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Ossining](https://expedia.ca/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.ca/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Ossining Car Rentals](https://expedia.ca/Car-Rentals-In-Ossining.d6190653.Car-Rental-Guide)[Ossining Vacation Packages](https://expedia.ca/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 # Find hotels in Ossining, NY from CA $155 - ![](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 ## Go beyond your typical stay in Ossining Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=HOT_TUB) Spa [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=SPA_ON_SITE) Pool [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=POOL) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=APART_HOTEL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&travelerType=family_friendly) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=PETS) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=COTTAGE) Villa [](https://www.expedia.ca/Hotel-Search?destination=Ossining%2C+New+York%2C+United+States+of+America®ionId=6190653&latLong=41.162872%2C-73.861526&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=VILLA) ## Check prices for these dates Tonight [Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-02&endDate=2026-01-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-03&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining hotels ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/f49620ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6b001cf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/005990bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Foliage at Westchester Manor - Near Sleepy Hollow [](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining CA $487 CA $1,187 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/1b1bee23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/30d2fd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/589f9bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windrose On Hudson [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) Ossining 8.2/10 Very good (106) "Clean room, staff were very welcoming" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Semaj CA $243 CA $271 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/58071d11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/150c0508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/5d58f7e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6550000/6541500/6541495/ab21b3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Peekskill -Lower Hudson Valley by IHG [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) Peekskill 9.2/10 Wonderful (1005) "Very comfortable beds,clean and breakfast was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dawn CA $167 CA $191 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/White-Plains-Hotels-Holiday-Inn-Express-Hotel-Suites-Peekskill-Hudson-Valley.h6541495.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/d4243906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Full Accessible](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/f5dd9616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/6eaf4dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/46000000/45610000/45603300/45603202/f3942ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Abbey Inn & Spa [](https://www.expedia.ca/White-Plains-Hotels-The-Abbey-Inn-Spa.h45603202.Hotel-Information) Peekskill 9.2/10 Wonderful (233) "Friendly staff and a great place to get away and recharge!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ariana CA $340 CA $452 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/White-Plains-Hotels-The-Abbey-Inn-Spa.h45603202.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/aa7f9d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/d1d794f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/7d4cc9d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/24000000/23010000/23005200/23005170/d05dbb0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cold Spring Hotel [](https://www.expedia.ca/Poughkeepsie-Hotels-Cold-Spring-Hotel.h23005170.Hotel-Information) Cold Spring 8.6/10 Excellent (155) "The owner is so warm and kind. The room was clean. Great place to stay for the weekend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wydayessi [](https://www.expedia.ca/Poughkeepsie-Hotels-Cold-Spring-Hotel.h23005170.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8400/8392/4ce7dec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/8400/8392/1757e0f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8400/8392/1107f714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8400/8392/edfef933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### J House Greenwich [](https://www.expedia.ca/Stamford-Hotels-J-House-Greenwich.h8392.Hotel-Information) Riverside 9.0/10 Wonderful (1003) "Nice hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aleksandr CA $335 CA $442 total includes taxes & fees Jan 10 - Jan 11 [](https://www.expedia.ca/Stamford-Hotels-J-House-Greenwich.h8392.Hotel-Information) ![Standard Room, 2 Queen Beds, Accessible (ADA)](https://images.trvl-media.com/lodging/5000000/4300000/4290600/4290545/9d24a068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, First or Second Floor](https://images.trvl-media.com/lodging/5000000/4300000/4290600/4290545/4b617c5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Building design](https://images.trvl-media.com/lodging/5000000/4300000/4290600/4290545/c20b7c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4300000/4290600/4290545/6ef5eea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Point Motel [](https://www.expedia.ca/Newburgh-Hotels-West-Point-Motel.h4290545.Hotel-Information) Highland Falls 8.6/10 Excellent (663) "Clean room and so close to West Point!! Great experience 👍 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SHANNON CA $137 CA $155 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Newburgh-Hotels-West-Point-Motel.h4290545.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/c0c1b35f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/023ab9be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/d09a0803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Thayer Hotel at West Point [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) West Point 9.0/10 Wonderful (675) "Location was great & staying at a historic hotel was delightful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bobby CA $209 CA $272 total includes taxes & fees Jan 3 - Jan 4 [](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/670b74a6.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) ![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) ![Room, 1 Queen Bed, Non Smoking (Stone Cottages at Bear Mountain)](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/42067525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Overlook Lodge at Bear Mountain [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) Bear Mountain 8.4/10 Very good (1008) "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 CA $152 CA $172 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/22000/21949/96fcaf69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/22000/21949/2677b974.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22000/21949/76854ba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/30000/22000/21949/fa990af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delamar Greenwich Harbor [](https://www.expedia.ca/Stamford-Hotels-Delamar-Greenwich-Harbor.h21949.Hotel-Information) Greenwich 9.4/10 Exceptional (959) "Great stay!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana CA $542 CA $644 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Stamford-Hotels-Delamar-Greenwich-Harbor.h21949.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/3a1a9879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/d7905bba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/2c18c9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, bed sheets](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/6806b0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Brewster [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information) Brewster 9.0/10 Wonderful (529) "Clean room. Great staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $174 CA $188 total includes taxes & fees Jan 7 - Jan 8 [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/c7d384a9.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) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/da52c924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/6459dee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Harriman Woodbury [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) Central Valley 9.2/10 Wonderful (1023) "Easy check in, clean room, very good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $134 CA $165 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/59004f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/9bf42dbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/d8f79ab8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/1fb7d2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express West Point by IHG [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-West-Point.h860232.Hotel-Information) Fort Montgomery 9.0/10 Wonderful (220) "Breakfast was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Todd CA $154 CA $174 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-West-Point.h860232.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/0ce6450f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 8:00 AM to 9:00 PM, free cabanas](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/4ed8dfa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Room with Kitchen (Private Entrance)](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/8561ada3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/76122822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heidi's Inn [](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) Brewster 8.8/10 Excellent (811) "The staff was nice and the room was clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mike CA $172 CA $186 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/a2060364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/f8bbba2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room | View from room](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b5096992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on the Hudson [](https://www.expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) Peekskill 7.0/10 Good (1004) "The location was very convenient. There is not a lot available in Peekskill and this place was very close to where we were going. The room was well cleaned and cared for the only drawback was that the heating unit was very, very noisy." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shelley CA $122 CA $140 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ![Deluxe Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/1c497b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/e714a3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/044fe424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LIV Hotel Bronx - Newly Built [](https://www.expedia.ca/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information) Bronx 7.2/10 Good (317) "Nice place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric CA $147 CA $173 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information) ![Indoor pool, seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/26100/26056/80d2d244.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/26100/26056/06079a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/1000000/30000/26100/26056/ae870ed9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26100/26056/6cf90e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marriott Park Ridge [](https://www.expedia.ca/Park-Ridge-Hotels-Marriott-Park-Ridge.h26056.Hotel-Information) Park Ridge 8.8/10 Excellent (880) "Great hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $196 CA $225 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Park-Ridge-Hotels-Marriott-Park-Ridge.h26056.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/5623b54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/ad434239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/w3998h2667x0y0-ce547fca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/21800/21786/28857133.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Montvale [](https://www.expedia.ca/Montvale-Hotels-Courtyard-By-Marriott-Montvale.h21786.Hotel-Information) Montvale 8.6/10 Excellent (658) "Clean, comfortable space. Friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) AMANDA CA $172 CA $197 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Montvale-Hotels-Courtyard-By-Marriott-Montvale.h21786.Hotel-Information) ![Premium Double Room | In-room dining](https://images.trvl-media.com/lodging/1000000/30000/26800/26729/a83d6afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Single Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/26800/26729/216600d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/30000/26800/26729/5efb8b6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/26800/26729/8f8c0f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn & Suites at West Point [](https://www.expedia.ca/Newburgh-Hotels-FairBridge-Inn-Suites-At-West-Point.h26729.Hotel-Information) Highland Falls 6.2/10 (797) "Excellent staff, super neat and clean room, very quiet and pleasant stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katherine CA $131 CA $155 total includes taxes & fees Jan 9 - Jan 10 [](https://www.expedia.ca/Newburgh-Hotels-FairBridge-Inn-Suites-At-West-Point.h26729.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3080000/3071700/3071699/623da1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/4000000/3080000/3071700/3071699/5e6f0d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, bathrobes, towels](https://images.trvl-media.com/lodging/4000000/3080000/3071700/3071699/30ac0c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/4000000/3080000/3071700/3071699/75ed5107.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lloyd Stamford, Tapestry Collection by Hilton [](https://www.expedia.ca/Stamford-Hotels-The-Lloyd-Stamford.h3071699.Hotel-Information) Downtown Stamford 8.8/10 Excellent (440) "Everything was just excellent. Perfect for our short stay and the staff was so kind. We are definitely returning here! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Meaghan CA $226 CA $260 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Stamford-Hotels-The-Lloyd-Stamford.h3071699.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=2026-01-16&endDate=2026-01-17®ionId=6190653&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FOssining-Hotels.d6190653.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Hotels.d6190653.Travel-Guide-Hotels) ## Learn more about Ossining Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront. [See all hotels in Ossining](https://www.expedia.ca/Hotel-Search?startDate=2026-01-16&endDate=2026-01-17&adults=2®ionId=6190653) ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=899&h=673&p=1&q=high) Photo by louann ohora ### Stay near popular Ossining attractions [](https://expedia.ca/Teatown-Lake-Reservation-Hotels.0-l553248621560458588-0.Travel-Guide-Filter-Hotels) ![Teatown Lake Reservation](https://mediaim.expedia.com/destination/2/f74defe22873b9089a9629b8811bc6eb.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Teatown Lake Reservation Explore the great outdoors at Teatown Lake Reservation, a lovely green space in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621560458588) [](https://expedia.ca/Sing-Sing-Correctional-Facility-Hotels.0-l553248621558038857-0.Travel-Guide-Filter-Hotels) #### Sing Sing Correctional Facility After visiting Sing Sing Correctional Facility, make a plan to see the other sights and activities in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621558038857) [](https://expedia.ca/Thomas-J-Watson-Research-Center-Hotels.0-l6087173-0.Travel-Guide-Filter-Hotels) #### Thomas J. Watson Research Center Learn about the local history of Ossining with a stop at Thomas J. Watson Research Center. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6087173) [](https://expedia.ca/Travelers-Rest-Hotels.0-l835647549279940608-0.Travel-Guide-Filter-Hotels) #### Travelers Rest After visiting Travelers Rest, make a plan to see the other sights and activities in Ossining. Amble around the area's parks or visit its monuments. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=835647549279940608) [](https://expedia.ca/Sing-Sing-Prison-Museum-Hotels.0-l553248621561873062-0.Travel-Guide-Filter-Hotels) #### Sing Sing Prison Museum You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561873062) [](https://expedia.ca/Ossining-Historical-Society-Hotels.0-l6207717-0.Travel-Guide-Filter-Hotels) #### Ossining Historical Society You can spend an afternoon studying the exhibits at Ossining Historical Society during your trip to Ossining. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6207717) ## More cheap stays in Ossining ![Comfort Inn Paramus - Hackensack](https://images.trvl-media.com/lodging/1000000/10000/6100/6017/b1a72c34_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn Paramus - Hackensack 50 N Rte 17 Paramus NJ CA $142 CA $162 total Jan 25 - Jan 26 includes taxes & fees 8.8/10 Excellent! (1,007 reviews) [](https://expedia.ca/Paramus-Hotels-Holiday-Inn-Express-Paramus.h6017.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Nanuet 20 Overlook Blvd Nanuet NY CA $140 CA $163 total Jan 4 - Jan 5 includes taxes & fees 8.2/10 Very Good! (1,006 reviews) [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Yonkers 160 Corporate Blvd Yonkers NY CA $144 CA $170 total Jan 22 - Jan 23 includes taxes & fees 8.2/10 Very Good! (1,700 reviews) [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baymont by Wyndham White Plains - Elmsford 540 Saw Mill River Rd Elmsford NY CA $161 CA $184 total Jan 25 - Jan 26 includes taxes & fees 8.2/10 Very Good! (1,463 reviews) [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![The Armon Stamford Hotel & Conference](https://images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Armon Stamford Hotel & Conference 2701 Summer St Stamford CT CA $190 CA $219 total Jan 4 - Jan 5 includes taxes & fees 7.6/10 Good! (713 reviews) [](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.Hotel-Information) ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Amsterdam Hotel 19 Clarks Hill Ave Stamford CT [Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F01%2F2026&endDate=17%2F01%2F2026&selected=20793&PinnedHotelID=20793&HadPinnedHotel=true®ionId=6190653) 8.4/10 Very Good! (1,731 reviews) [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ## Hotels in Ossining with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 1 properties [](https://expedia.ca/5Star-Ossining-Hotels.s50-0-d6190653.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 56 properties [](https://expedia.ca/4Star-Ossining-Hotels.s40-0-d6190653.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 140 properties [](https://expedia.ca/3Star-Ossining-Hotels.s30-0-d6190653.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 237 properties [](https://expedia.ca/2Star-Ossining-Hotels.s20-0-d6190653.Travel-Guide-Filter-Hotels) ## Find out more about Ossining ### Top reasons to visit Ossining - **Scenic Outdoor Activities:** Enjoy serene walks in the Ridge Preserve and explore urban parks and nature reserves. - **Family-Friendly Attractions:** Ossining offers numerous activities perfect for families, ensuring a fun-filled vacation. - **Cultural Experiences:** Immerse yourself in the local culture by visiting nearby colleges and engaging with the vibrant community. - **Shopping Opportunities:** Shop at the Woodbury Commons Premium Outlets for a delightful retail experience. - **Diverse Accommodation:** Choose from charming bed and breakfasts to modern hotels, catering to various preferences. ### Find great hotels near Ossining Ossining offers a delightful variety of lodging options, from charming bed and breakfasts to modern hotels tailored for business travellers. Whether you’re looking for pet-friendly accommodations or a welcoming environment for LGBTQIA guests, you'll find the ideal spot to unwind. Explore the best hotels in Ossining and nearby areas to enjoy a truly memorable vacation experience. - **[Ramada by Wyndham Rochelle Park Near Paramus: ](https://www.expedia.ca/Rochelle-Park-Hotels-Ramada-By-Wyndham-Rochelle-Park-Near-Paramus.h1087.Hotel-Information)** Situated 33.8km from Ossining, the Ramada by Wyndham Rochelle Park Near Paramus offers a welcoming retreat for leisure and business travellers alike. Guests can enjoy complimentary breakfast daily, including a buffet selection, while the on-site restaurant provides further dining options. The hotel features a fitness facility for those keen on staying active during their stay. With nearby attractions such as shopping districts and metro stations, guests have easy access to explore the local area. Entertainment options including premium TV channels ensure a relaxing evening after a busy day. - **[Amsterdam Hotel: ](https://www.expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information)** Located 30.6km from Ossining, the Amsterdam Hotel is ideal for business travellers seeking a focused environment. This hotel is equipped with multiple meeting rooms and a fully serviced business centre, making it perfect for those attending conferences or corporate meetings. Its proximity to the business district allows easy access to various corporate offices. The professional atmosphere combined with essential amenities ensures a seamless experience for working guests who appreciate comfort and convenience. - **[Baymont by Wyndham White Plains - Elmsford: ](https://www.expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information)** Just 11.3km from Ossining, the Baymont by Wyndham White Plains - Elmsford is a family-friendly hotel that also caters to the needs of business travellers. With a 24-hour accessible business centre and meeting rooms, it provides a productive space for work-related activities. Families will appreciate the complimentary cribs and first aid kits, ensuring a safe and comfortable stay for children. The hotel's welcoming atmosphere and convenient location make it an excellent choice for both leisure and business trips. ### Where to stay in and around Ossining Ossining, New York, offers a delightful blend of family-friendly activities and serene outdoor experiences. Explore the cozy getaways in the Ossining area and enjoy leisurely walks in the Ridge Preserve, where nature's beauty unfolds. For shopping enthusiasts, the Woodbury Commons Premium Outlets are just a short drive away. This charming city provides a perfect location for relaxation, romance, and creating lasting memories with loved ones. - **[Crotonville: ](https://www.expedia.ca/Crotonville-Hotels.d553248635975868892.Travel-Guide-Hotels)** Nestled within the Ossining area, Crotonville is a quaint village that offers a rich cultural experience. While the number of visitors remains consistent year-round, springtime (April to May) and the holiday season (December) see the highest influx of tourists. Crotonville is perfect for families and outdoor enthusiasts, with attractions including shopping centres and educational venues. Notable nearby landmarks feature historic houses and buildings, providing visitors with a glimpse into the area's past while enjoying its vibrant community atmosphere. - **[Maryknoll: ](https://www.expedia.ca/Maryknoll-Hotels.d3000449058.Travel-Guide-Hotels)** Just 3.2km from Ossining, Maryknoll is a charming city that is ideal for sports lovers and families alike. The peak travel months are typically in the summer (July to August) and the festive season (December). Visitors can engage in various activities, including baseball and soccer, making it a lively destination for outdoor fun. The urban parks and event venues enhance the experience, offering green spaces for relaxation and community gatherings. With its blend of recreational opportunities and historical sites, Maryknoll is a delightful stop on your journey. - **[Briarcliff Manor: ](https://www.expedia.ca/Briarcliff-Manor-Hotels.d7040.Travel-Guide-Hotels)** A mere 3.2km from Ossining, Briarcliff Manor is a picturesque city that attracts families and culture enthusiasts. The best times to visit are in January and during the spring months (April to May). The city boasts numerous shopping areas and educational institutions, ensuring a fulfilling experience for all ages. Notable attractions include serene lakes and historic places, providing a tranquil backdrop for exploration. Briarcliff Manor's charm lies in its combination of outdoor activities and rich cultural heritage, making it a must-visit location. ### Things to do near Ossining Ossining, New York, offers a delightful blend of outdoor and family-friendly activities, making it perfect for a city-themed vacation. Visitors can enjoy skiing and explore local shopping areas. Additionally, nearby Tarrytown is known for picturesque wedding venues, adding a romantic touch to your trip. With its scenic beauty and vibrant community, Ossining promises a memorable experience for all travellers. **Shopping** In Ossining, check out [Rockland Bakery](https://www.expedia.ca/Rockland-Bakery-Hotels.0-l553248621532664487-0.Travel-Guide-Filter-Hotels) for local treats, only 12.9km away. If you're up for a drive, visit [Westchester's Ridge Hill](https://www.expedia.ca/Westchesters-Ridge-Hill-Hotels.0-l553248621558114293-0.Travel-Guide-Filter-Hotels), 22.5km away, for a variety of shops and family-friendly vibes. For an extensive experience, the [Woodbury Common Premium Outlets](https://www.expedia.ca/Woodbury-Common-Premium-Outlets-Hotels.0-l6127054-0.Travel-Guide-Filter-Hotels) is 27.4km away. **Recreation** Experience the vibrant atmosphere at [Tarrytown Music Hall](https://www.expedia.ca/Tarrytown-Music-Hall-Hotels.0-l6211022-0.Travel-Guide-Filter-Hotels), where live performances uplift your spirit. For relaxation, visit [Hardscrabble Wilderness Area](https://www.expedia.ca/Hardscrabble-Wilderness-Area-Hotels.0-l553248621587293678-0.Travel-Guide-Filter-Hotels), a serene retreat perfect for nature walks. Enjoy the outdoors at [Rockland Lake State Park Championship Golf Course](https://www.expedia.ca/Rockland-Lake-State-Park-Championship-Golf-Course-Hotels.0-l6253469-0.Travel-Guide-Filter-Hotels), offering a refreshing blend of sport and scenic beauty. **Adventure** At [Palisades Climb Adventure](https://www.expedia.ca/Palisades-Climb-Adventure-Hotels.0-l553248621532664490-0.Travel-Guide-Filter-Hotels), experience the thrill of ziplining and navigating an exhilarating ropes course surrounded by nature, located 11.3km from Ossining. For karting enthusiasts, Grand Prix New York offers high-speed fun, just 12.9km away. Explore the scenic Orange Trailhead, a fantastic outdoor access point, also 11.3km from Ossining. **Nightlife** Experience the vibrant nightlife in Ossining by enjoying a show at the [Westchester Broadway Theatre](https://www.expedia.ca/Westchester-Broadway-Theatre-Hotels.0-l6183430-0.Travel-Guide-Filter-Hotels), just 11.3km away. For some fun, visit [Lucky Strike](https://www.expedia.ca/Lucky-Strike-Hotels.0-l553248621532664489-0.Travel-Guide-Filter-Hotels) ArcadeAdventureZone, also 11.3km away. If you're in the mood for a film, head to [Maritime IMAX](https://www.expedia.ca/Maritime-IMAX-Hotels.0-l6129064-0.Travel-Guide-Filter-Hotels), located 38.6km away for an entertaining evening. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Ossining To save money during your visit to Ossining, consider travelling from January to March when hotel prices are lower. Book your accommodation about a month in advance for the best rates, with Sundays being the cheapest day to stay. Use Expedia to find last-minute deals and compare prices easily. You can also save by bundling your hotel with flights and activities. For public transport, take advantage of the local bus system to navigate the area affordably. Finally, explore free activities like parks and local events to make the most of your trip without overspending. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Ossining are January to March, where the prices are slightly lower. This is in comparison to September to October and December, where prices are slightly higher. - **The best time to book a hotel:** Book your hotel in Ossining about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Ossining is Sunday. The most expensive day to stay in Ossining is Saturday. - **Find cheap hotels on Expedia:** Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from the lowest to the highest, making it easy to find the most affordable accommodations first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking. - **Consider bundling your trip:** You can save money by combining your Ossining hotel reservation with your flights and activities through an Expedia package. ### Find the best attractions in and around Ossining Ossining, New York, offers a delightful blend of outdoor activities and family-friendly attractions, making it ideal for a city-themed getaway. Explore urban parks, nature reserves, and local colleges while immersing yourself in the region's culture. Whether you're seeking a tranquil day outdoors or a cultural experience, Ossining caters to diverse interests, ensuring a memorable vacation for every traveller. - **[Van Cortlandt Manor: ](https://www.expedia.ca/Van-Cortlandt-Manor-Hotels.0-l6207691-0.Travel-Guide-Filter-Hotels)** Experience the charm of this historic house, where you can explore beautifully preserved rooms and stunning gardens. Immerse yourself in the culture and history of the Hudson Valley, showcasing the region’s colonial past. - **[Sing Sing Correctional Facility: ](https://www.expedia.ca/Sing-Sing-Correctional-Facility-Hotels.0-l553248621558038857-0.Travel-Guide-Filter-Hotels)** This historic prison offers unique insights into the justice system and its historical significance. Take a guided tour to learn about its infamous past and the stories of those who resided within its walls. - **[Croton Point Park: ](https://www.expedia.ca/Croton-Point-Park-Hotels.0-l6093731-0.Travel-Guide-Filter-Hotels)** Perfect for families, this urban park features expansive green spaces, hiking trails, and picnic areas. Enjoy outdoor activities while taking in breathtaking views of the Hudson River, making it a delightful escape from city life. ### Best time to go to Ossining The best time to visit Ossining is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 30.0°F (-1.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 31.6°F (-0.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 38.8°F (3.8°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 49.8°F (9.9°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 60.1°F (15.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 68.9°F (20.5°C) | Light Rain | Mostly Sunny | Average | Average | | July | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.9°F (23.3°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.9°F (19.4°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 56.1°F (13.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 44.2°F (6.8°C) | Light Rain | Mostly Sunny | Average | Average | | December | 36.3°F (2.4°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High | ### The nearest major airports for your trip to Ossining When planning your visit to Ossining, New York, you can choose from three major airports. John F. Kennedy International Airport ([JFK](https://www.expedia.ca/John-F-Kennedy-Intl-Airport-Hotels.0-aJFK-0.Travel-Guide-Filter-Hotels)) is located 57.9km away, with nearby hotels such as the 5-star [Arlo Williamsburg](https://www.expedia.ca/New-York-Hotels-The-Williamsburg-Hotel.h16007579.Hotel-Information) and [The William Vale](https://www.expedia.ca/New-York-Hotels-The-William-Vale.h11971622.Hotel-Information), both 17.7km from the airport. Newark Liberty International Airport ([EWR](https://www.expedia.ca/Newark-Liberty-Intl-Airport-Airport-Hotels.0-aEWR-0.Travel-Guide-Filter-Hotels)) is 59.5km distant, featuring luxurious options like [The Dominick](https://www.expedia.ca/New-York-Hotels-The-Dominick.h21783007.Hotel-Information) and [The Wall Street Hotel](https://www.expedia.ca/New-York-Hotels-The-Wall-Street-Hotel.h55444869.Hotel-Information), both 14.5km away. Lastly, LaGuardia Airport ([LGA](https://www.expedia.ca/LaGuardia-Airport-Hotels.0-aLGA-0.Travel-Guide-Filter-Hotels)) is 43.5km from Ossining, with excellent accommodations like [Virgin Hotels New York City](https://www.expedia.ca/New-York-Hotels-Virgin-Hotels-New-York-City.h87406830.Hotel-Information) and [The Carlyle](https://www.expedia.ca/New-York-Hotels-The-Carlyle.h40553.Hotel-Information), both just 5-9.7km from the airport. Each airport offers convenient transportation options to Ossining. ## Recent reviews of Ossining hotels ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 5/5 Excellent "This is an older affordable hotel. The room was very clean. Everything worked except the tub stopper. The staff is friendly and helpful. There is free onsite parking. A basic continental breakfast. It is convenient to the metro north station. The neighborhood is quiet and safe. Fast food and convenience stores are walkable." A verified traveller stayed at Amsterdam Hotel Posted 23 hours ago [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 5/5 Excellent "Clean room." A verified traveller stayed at Royal Regency Hotel Posted 2 days ago [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg) ### Hampton Inn & Suites Yonkers 5/5 Excellent "Yes all was good " A verified traveller stayed at Hampton Inn & Suites Yonkers Posted 2 days ago [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.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 5/5 Excellent "Nice, professional staff, clean room & a convenient location for our needs. " A verified traveller stayed at Hotel NoMa, Trademark Collection by Wyndham Posted 2 days ago [](https://expedia.ca/White-Plains-Hotels-Radisson-Hotel-New-Rochelle.h1088006.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 5/5 Excellent "." A verified traveller stayed at Sonesta White Plains Downtown Posted 2 days ago [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Ardsley Acres Hotel Westchester](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 5/5 Excellent "Great hospitality and comfort" A verified traveller stayed at Ardsley Acres Hotel Westchester Posted 3 days ago [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Armoni Inn & Suites](https://images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 5/5 Excellent "Easy to use" A verified traveller stayed at Armoni Inn & Suites Posted 3 days ago [](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.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 5/5 Excellent "Very convenient" A verified traveller stayed at Hampton Inn White Plains/Tarrytown Posted 3 days ago [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 5/5 Excellent "Clean, quiet room, helpful staff, beautiful restaurant/bar area." A verified traveller stayed at Hyatt Regency Greenwich Posted 3 days ago [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Ossining? > As you plan your trip, keep in mind that the peak tourist season in Ossining tends to run from June through October. September, in particular, features a delightful blend of outdoor activities and local events, such as farmers' markets and community festivals, which allow you to immerse yourself in the local culture. The comfortable temperatures make it superb for leisurely strolls along the waterfront or hiking in the nearby parks, where you can enjoy the breathtaking fall foliage. > > > For those seeking a more tranquil experience, October can also be a lovely time to visit. The autumn colours create a picturesque setting that is superb for photography and outdoor exploration. Additionally, you may find that accommodations and attractions offer more competitive pricing as the summer crowds begin to thin out. ### Where can I find the best nightlife in Ossining? > For those seeking a night out, the downtown area features a few local pubs and casual dining spots that often host live music or trivia nights. Venues like the Sing Sing Kill Brewery provide a great experience with craft beers brewed on-site, superb for enjoying a relaxed evening with friends. > > > If you're in the mood for a bit more excitement, nearby towns like Tarrytown and Sleepy Hollow boast a wider range of nightlife options, including bars, restaurants, and live music venues that can easily be reached by a short drive. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Ossining hotel booking with Expedia? ### How much is the nightly rate at a Ossining hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [4 Star Hotels in Briarcliff Manor ](https://www.expedia.ca/4Star-Briarcliff-Manor-Hotels.s40-0-d7040.Travel-Guide-Filter-Hotels) - [Hotels near NYC-All Airports ](https://www.expedia.ca/All-Airports-Airport-Hotels.0-aNYC-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Briarcliff Manor ](https://www.expedia.ca/Briarcliff-Manor-Apart-Hotels.d7040-aaApartHotels.Travel-Guide-Accommodation) - 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