Title: Ossining Travel Guide: Best of Ossining, New York Travel 2026 | Expedia.co.uk [Hotels in Ossining](https://expedia.co.uk/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Holiday Rentals in Ossining](https://expedia.co.uk/Ossining-Holiday-Rentals.d6190653.Travel-Guide-HolidayRentals)[Ossining Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Ossining.d6190653.Car-Hire-Guide)[Ossining Holidays](https://expedia.co.uk/Ossining.d6190653.Holidays-City-Breaks) # Ossining Travel Guide ## Tourist 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 - Top hotels in Ossining - Top Holiday 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 £147 15 Feb - 16 Feb includes taxes & fees Stay at this business-friendly hotel in Ossining. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Van Cortlandt Manor and Croton ... 8.2/10 Very Good! (109 reviews) Staff were very pleasant. Reviewed on 26 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=112806652&PinnedHotelID=112806652&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 £154 15 Feb - 16 Feb includes taxes & fees Stay at this business-friendly hotel in White Plains. Enjoy free Wi-Fi, breakfast (surcharge) and free airport pick-up. Our guests praise the bar and the helpful ... 8.6/10 Excellent! (1,269 reviews) Nice staff, clean hotel. Reviewed on 3 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=6190653) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Nanuet 425 E Route 59 Nanuet NY £87 22 Feb - 23 Feb includes taxes & fees Stay at this golf hotel in Nanuet. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the pool and the helpful staff in their reviews. ... 8.8/10 Excellent! (1,055 reviews) The hallways are nice but the wallpaper is coming off in the rooms. If that kinda stuff bothers you. Pet friendly hotel so I had a dog barking while I was trying to sleep. I asked for a little grace due to the noise and the front desk didn’t seem to care. Oh well. Warm pool for kids and hot tub. Reviewed on 2 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6190653) [See all 1,334 properties in Ossining](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=09%2F02%2F2026&endDate=10%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 Stay at this family-friendly holiday home in Ossining. Enjoy free Wi-Fi, private pools and a water park. Popular attractions Snowden Avenue Park and Ossining ... 9.2/10 Wonderful! (7 reviews) Super fun location! Host was very helpful. The house is very comfortable for large groups Reviewed on 1 Dec 2025 [](https://expedia.co.uk/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 Stay at this 4-star business-friendly aparthotel in Stamford. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their ... 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 19 Jan 2026 [](https://expedia.co.uk/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 Stay at this business-friendly apartment in White Plains. Enjoy free Wi-Fi, an outdoor pool and valet parking (surcharge). Popular attractions Galleria at White ... 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 12 Dec 2025 [](https://expedia.co.uk/White-Plains-Hotels-Global-Luxury-Suites-White-Plains.h74125740.Hotel-Information) [See all properties in Ossining](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-08&endDate=2026-02-09)[8 Feb - 9 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-08&endDate=2026-02-09) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-09&endDate=2026-02-10)[9 Feb - 10 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=2026-02-09&endDate=2026-02-10) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[13 Feb - 15 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6190653&startDate=13%2F02%2F2026&endDate=15%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 quaint area's riverfront and enjoy its top-notch restaurants. [](https://expedia.co.uk/Teatown-Lake-Reservation-Ossining.d553248621560458588.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.co.uk/Travelers-Rest-Ossining.d835647549279940608.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.co.uk/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Attraction) #### Thomas J. Watson Research Center Learn about the local history of Ossining when you take a trip to Thomas J. Watson Research Center. Stroll along the riverfront in this family-friendly area or visit its top-notch restaurants. [](https://expedia.co.uk/Thomas-J-Watson-Research-Center-Ossining.d6087173.Attraction) #### Sing Sing Prison Museum You can spend time studying the exhibits at Sing Sing Prison Museum in Ossining. Amble around this quaint area's riverfront and enjoy its top-notch restaurants. [](https://expedia.co.uk/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.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 visit its top-notch restaurants. [](https://expedia.co.uk/Nelson-Park-Ossining.d553248621557931331.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 - Cities near Ossining - Places of interest [Briarcliff Manor](https://expedia.co.uk/Briarcliff-Manor.dx7040)[Mount Kisco](https://expedia.co.uk/Mount-Kisco.dx8984)[Chappaqua](https://expedia.co.uk/Chappaqua.dx88470)[Croton-on-Hudson](https://expedia.co.uk/Croton-On-Hudson.dx183658)[Yorktown Heights](https://expedia.co.uk/Yorktown-Heights.dx6338662) - [Woodbury Common Premium Outlets ](https://expedia.co.uk/Woodbury-Common-Premium-Outlets-Central-Valley.d6127054.Attraction) - [Bear Mountain State Park ](https://expedia.co.uk/Bear-Mountain-State-Park-New-York.d6127050.Attraction) - [Westchester County Center ](https://expedia.co.uk/Westchester-County-Center-White-Plains.d6066133.Attraction) - [Empire City Casino ](https://expedia.co.uk/Empire-City-Casino-Southeast-Yonkers.d6172190.Attraction) - [Stamford Town Center ](https://expedia.co.uk/Stamford-Town-Center-Downtown-Stamford.d6125753.Attraction) - [New Roc City ](https://expedia.co.uk/New-Roc-City-Downtown-Rochelle.d6179751.Attraction) - [Lyndhurst Mansion ](https://expedia.co.uk/Lyndhurst-Mansion-Tarrytown.d6093725.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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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