Title: Visit Ossining: 2026 Travel Guide for Ossining, New York | Expedia.com [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) # Ossining, NY ## Travel Guide ![Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York. ](https://images.trvl-media.com/place/6190653/d6b06ec0-5d8e-4f01-b77d-2dc521a46ea1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Westchester, NY, USA: A rail bridge spans an inlet on the Hudson River, with St. Augustine’s Roman Catholic Church, Ossining, NY, in the background. ](https://images.trvl-media.com/place/6190653/472c72dd-f23e-418c-a8d2-105b7dd45c20.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![The start of the Bergmann boardwalk at Teatown Reservation in Westchester County, New York](https://images.trvl-media.com/place/6190653/480e4d5f-1754-4fe2-b689-22410edfde5f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![rows of Victorian building sit t side by side in downtown Ossining, New York](https://images.trvl-media.com/place/6190653/816a8f53-2df2-4e4a-9d35-0719e8170a31.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Sunset at the Ossining waterfront](https://images.trvl-media.com/place/6190653/9ea2ffd5-f98e-40ce-8c31-b0c6a6a646c1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Ossining Things to do ![](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=DX_SPRING_PROMO_6190653) - Ossining Hotel Deals - Vacation Rentals in Ossining ![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Windrose On Hudson 1 Shady Lane Farm Road Ossining NY $181 nightly $202 total Apr 1 - Apr 2 Total with taxes and fees Book a stay at this business-friendly hotel in Ossining. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Van Cortlandt Manor and ... 8.4/10 Very Good! (118 reviews) My bathroom was dirty with crap on the wall , floor around toilet Reviewed on Mar 12, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=112806652&PinnedHotelID=112806652&HadPinnedHotel=true®ionId=6190653) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham White Plains - Elmsford 540 Saw Mill River Rd Elmsford NY $131 nightly $150 total Mar 30 - Mar 31 Total with taxes and fees Book a stay at this business-friendly hotel in Elmsford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 8.2/10 Very Good! (1,607 reviews) Drop off area is a nightmare. Property smells like weed everywhere. Rooms were small and didn’t have much in the way of furniture. Overall it’s basically a small improvement over a motor lodge. Reviewed on Mar 13, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F30%2F2026&endDate=3%2F31%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=6190653) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/c532560d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Nanuet 425 E Route 59 Nanuet NY $106 nightly $123 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ... 9/10 Wonderful! (1,077 reviews) Nice hotel all around. Reviewed on Mar 14, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6190653) [See all 1,326 properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F16%2F2026&endDate=3%2F17%2F2026®ionId=6190653) 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. ![Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining NY Stay at this vacation home in Ossining. Enjoy free WiFi, private pools, and a garden. Popular attractions Nelson Park and Sing Sing Prison Museum are located ... 9.2/10 Wonderful! (7 reviews) Super fun location! Host was very helpful. The house is very comfortable for large groups Reviewed on Dec 1, 2025 [](https://expedia.com/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![Stamford Suites](https://images.trvl-media.com/lodging/1000000/30000/25900/25900/b7db331c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stamford Suites 720 Bedford St Stamford CT Book a stay at this business-friendly aparthotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ... [](https://expedia.com/Stamford-Hotels-Stamford-Suites.h25900.Hotel-Information) ![Global Luxury Suites White Plains](https://images.trvl-media.com/lodging/75000000/74130000/74125800/74125740/343ab6e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Global Luxury Suites White Plains 57 Bank St White Plains NY Book a stay at this business-friendly apartment in White Plains. Enjoy free WiFi, an outdoor pool, and valet parking (surcharge). Popular attractions Westchester ... 6.8/10 (40 reviews) Please stay away from this horrible place!!! I have travelled all over the world but never dealt with such terrible company and their property. Reviewed on Mar 14, 2026 [](https://expedia.com/White-Plains-Hotels-Global-Luxury-Suites-White-Plains.h74125740.Hotel-Information) [See all properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6190653&sort=VACATION_RENTAL) 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. ## Check Ossining hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-03-15&endDate=2026-03-16)[Mar 15 - Mar 16](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-03-15&endDate=2026-03-16) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-03-16&endDate=2026-03-17)[Mar 16 - Mar 17](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-03-16&endDate=2026-03-17) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026) ### Popular places to visit ![Lovely spot in Westchester, NY](https://images.trvl-media.com/place/553248621560458588/f1c654af-0d4d-4605-9da4-0e6de2024125.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. [](https://expedia.com/Teatown-Lake-Reservation-Ossining.d553248621560458588.Vacation-Attraction) ![Rest stop area beside interstate highway where travelers rest and sight see Tioga Reservoir and Dam in Pennsylvania New York state border](https://images.trvl-media.com/place/835647549279940608/a2b5cdb4-0d08-4c9d-b8b4-e47aa8caa5da.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Travelers-Rest-Ossining.d835647549279940608.Vacation-Attraction) #### 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. [](https://expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction) #### Sing Sing Prison Museum You can spend time browsing the exhibits at Sing Sing Prison Museum during your travels in Ossining. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants. [](https://expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction) #### 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. [](https://expedia.com/Thomas-J-Watson-Research-Center-Ossining.d6087173.Vacation-Attraction) #### Nelson Park Nelson Park is just one of the places to see in Ossining, so why not enjoy the other things to explore during your travels? Stroll along the riverfront in this family-friendly area, or check out its top-notch restaurants. [](https://expedia.com/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction) ## Cities near Ossining ![Stone bridge in Rockefeller State Park over the Pocantico River in autumn](https://images.trvl-media.com/place/7040/56c49846-1e91-46dc-9c8b-5e16bbfa762f.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Briarcliff Manor ![Mount Kisco Train Station, Westchester, New York, snow, ](https://images.trvl-media.com/place/8984/0ed5affd-7834-4854-bad9-59a4774033d3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Mount Kisco ![New Croton Dam, Croton-On-Hudson, Croton Gorge Park, NY. USA](https://images.trvl-media.com/place/183658/bacd69ec-8a6e-411e-9107-e3c7591a0652.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Croton-on-Hudson ![Late afternoon aerial autumn image of the area surrounding the Yorktown Heights, NY, USA 10-16-2024](https://images.trvl-media.com/place/6338662/af34e37e-44d4-4788-b8d3-d7dabc7141b3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Yorktown Heights ## 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) - [Hotels near Ossining Station ](https://www.expedia.com/Ossining-Station-Hotels.d6338907.Travel-Guide-Hotels) - [Hotels near Depot Square ](https://www.expedia.com/Depot-Square-Hotels.0-l553248621558038859-0.Travel-Guide-Filter-Hotels) - 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[Flights to New York ](https://www.expedia.com/Cheap-Flights-To-New-York.d178293.Travel-Guide-Flights) - [Flights to Maryknoll ](https://www.expedia.com/Cheap-Flights-To-Maryknoll.d3000449058.Travel-Guide-Flights) - [Flights to Briarcliff Manor ](https://www.expedia.com/Cheap-Flights-To-Briarcliff-Manor.d7040.Travel-Guide-Flights) - [Flights from Briarcliff Manor ](https://www.expedia.com/lp/flights/7040/flights-from-briarcliff-manor) - [Flights from Westchester County ](https://www.expedia.com/lp/airports/hpn/flights-from-westchester-county-airport) - [Flights to Croton-on-Hudson ](https://www.expedia.com/Cheap-Flights-To-Croton-On-Hudson.d183658.Travel-Guide-Flights) - [Flights from Croton-on-Hudson ](https://www.expedia.com/lp/flights/183658/flights-from-croton-on-hudson) - [Dallas to Croton-on-Hudson ](https://www.expedia.com/lp/flights/178253/183658/dallas-to-croton-on-hudson) - [Sing Sing Prison Museum ](https://www.expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction) - [Snowden Avenue Park ](https://www.expedia.com/Snowden-Avenue-Park-Ossining.d553248621558038861.Vacation-Attraction) - [Depot Square ](https://www.expedia.com/Depot-Square-Ossining.d553248621558038859.Vacation-Attraction) - [Sing Sing Correctional Facility ](https://www.expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction) - [Nelson Park ](https://www.expedia.com/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction) - [Louis Engel Waterfront Park ](https://www.expedia.com/Louis-Engel-Waterfront-Park-Ossining.d553248621587293691.Vacation-Attraction) - [Visit Maryknoll ](https://www.expedia.com/Maryknoll.dx3000449058) - [Visit Briarcliff Manor ](https://www.expedia.com/Briarcliff-Manor.dx7040) - [Croton Point Park ](https://www.expedia.com/Croton-Point-Park-Croton-on-Hudson.d6093731.Vacation-Attraction) - [Van Cortlandt Manor ](https://www.expedia.com/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) - [Corning Tower ](https://www.expedia.com/Corning-Tower-Croton-on-Hudson.d553248621532664094.Vacation-Attraction) - 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