Title: Visit Ossining: Best of Ossining Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Ossining](https://expedia.ca/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[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) # Ossining ## 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) ![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) ![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 - Ossining Hotel Deals - Vacation Rentals in Ossining ![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Windrose On Hudson 1 Shady Lane Farm Road Ossining NY CA $219 CA $243 total Feb 15 - Feb 16 includes taxes & 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 ... 8.2/10 Very Good! (109 reviews) Staff were very pleasant. Reviewed on Jan 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%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 Fully refundableReserve now, pay when you stay CA $168 CA $192 total Feb 22 - Feb 23 includes taxes & 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! (1,534 reviews) Great Reviewed on Feb 7, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=6190653) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sonesta White Plains Downtown 66 Hale Ave White Plains NY CA $206 CA $281 total Feb 15 - Feb 16 includes taxes & fees Book a stay at this business-friendly hotel in White Plains. Enjoy free WiFi, breakfast (surcharge), and free airport pick-up. Our guests praise the bar and ... 8.6/10 Excellent! (1,273 reviews) Staff were courteous and helpful. Great location! Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=6190653) [See all 1,330 properties in Ossining](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=12%2F02%2F2026&endDate=13%2F02%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/102000000/101860000/101852400/101852343/76b5d504_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! Ossining NY Book a stay at this family-friendly vacation home in Ossining. Enjoy free WiFi, private pools, and a water park. Popular attractions Snowden Avenue Park and ... 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.ca/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![Stamford Suites](https://images.trvl-media.com/lodging/1000000/30000/25900/25900/3cf11d68_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. ... 6.4/10 (98 reviews) Nice clean rooms the bedding was comfortable, it smelled good walking in, I will be staying in this hotel in the next time I'm in Stamford. Reviewed on Jan 19, 2026 [](https://expedia.ca/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 Galleria ... 6.8/10 (38 reviews) Great location, spacious apartment and clean. The public areas like the hallway needed vacuuming but everything else was great. Reviewed on Dec 12, 2025 [](https://expedia.ca/White-Plains-Hotels-Global-Luxury-Suites-White-Plains.h74125740.Hotel-Information) [See all properties in Ossining](https://expedia.ca/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.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-11&endDate=2026-02-12)[Feb 11 - Feb 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-11&endDate=2026-02-12) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-12&endDate=2026-02-13)[Feb 12 - Feb 13](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-12&endDate=2026-02-13) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[Feb 20 - Feb 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=20%2F02%2F2026&endDate=22%2F02%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.ca/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.ca/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 family-friendly area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.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.ca/Thomas-J-Watson-Research-Center-Ossining.d6087173.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 quaint area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.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 quaint area, or check out its top-notch restaurants. [](https://expedia.ca/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction) ## Cities near Ossining ![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 ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Maryknoll - Cities near Ossining - Places of interest [Croton-on-Hudson](https://expedia.ca/Croton-On-Hudson.dx183658)[Yorktown Heights](https://expedia.ca/Yorktown-Heights.dx6338662)[Maryknoll](https://expedia.ca/Maryknoll.dx3000449058)[Crotonville](https://expedia.ca/Crotonville.dx553248635975868892)[Sparta](https://expedia.ca/Sparta.dx950888526921347072) - [Woodbury Common Premium Outlets ](https://expedia.ca/Woodbury-Common-Premium-Outlets-Central-Valley.d6127054.Vacation-Attraction) - [NewYork-Presbyterian - Westchester Hospital ](https://expedia.ca/NewYork-Presbyterian-Westchester-Hospital-Bronxville.d553248621591002858.Vacation-Attraction) - [Bear Mountain State Park ](https://expedia.ca/Bear-Mountain-State-Park-New-York.d6127050.Vacation-Attraction) - [Westchester County Center ](https://expedia.ca/Westchester-County-Center-White-Plains.d6066133.Vacation-Attraction) - [Empire City Casino ](https://expedia.ca/Empire-City-Casino-Southeast-Yonkers.d6172190.Vacation-Attraction) - [Paramus Park Mall ](https://expedia.ca/Paramus-Park-Mall-Paramus.d6079833.Vacation-Attraction) - [Lyndhurst Mansion ](https://expedia.ca/Lyndhurst-Mansion-Tarrytown.d6093725.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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