Title: Ossining Vacation Packages 2026 from $438 | Expedia.com [Ossining Travel Guide](https://expedia.com/Ossining.dx6190653)[Hotels in Ossining](https://expedia.com/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Vacation Rentals in Ossining](https://expedia.com/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.com/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Car Rentals in Ossining](https://expedia.com/Car-Rentals-In-Ossining.d6190653.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6190653/d6b06ec0-5d8e-4f01-b77d-2dc521a46ea1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Ossining Vacations from $438 ## Book a Hotel + Flight or Car together to unlock savings ## Your Ossining Vacation Experience the energy and excitement of Ossining with a tailor-made Ossining vacation package. From its rich history to its spectacular views and beyond, you'll never have a boring moment in this city. Eager to explore your surroundings? [Tarrytown Music Hall](https://www.expedia.com/Tarrytown-Music-Hall-Tarrytown.d6211022.Vacation-Attraction), [Van Cortlandt Manor](https://www.expedia.com/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) and [Sing Sing Correctional Facility](https://www.expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction) are some of the leading places to visit during a trip to Ossining. Browse Expedia's extensive range of travel options and begin planning your perfect vacation to Ossining now. ## The Latest Ossining vacation packages Price found within the past 48 hours. Click for updated prices. ![OYO Times Square](https://images.trvl-media.com/lodging/1000000/10000/6700/6697/b192d80d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### OYO Times Square Manhattan Save 100% on your flight $438 per person Apr 30 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 7.2/10 Good! (1,617 reviews) Very small but clean room!! Staff was super friendly and helpful!:) Reviewed on Feb 22, 2026 ![The Towers at Lotte New York Palace](https://images.trvl-media.com/lodging/5000000/4200000/4195300/4195208/02d4f5a0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Towers at Lotte New York Palace Manhattan $1,880 per person May 12 - May 17 found 10 hours ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (638 reviews) Close to major shopping and multiple dining options Reviewed on Jan 21, 2026 ![Loews Regency New York Hotel](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Loews Regency New York Hotel Manhattan $1,558 per person May 12 - May 17 found 13 hours ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,002 reviews) Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready. Reviewed on Feb 24, 2026 ![Hotel Riu Plaza New York Times Square](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/8c07d74e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza New York Times Square Manhattan Save 100% on your flight $786 per person May 14 - May 17 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,790 reviews) Room was great. Buffet breakfast was amazing with so many options. Love the fact that a bar and coffee shop are downstairs next to the lobby. Reviewed on Feb 24, 2026 ![Hotel Riu Plaza Manhattan Times Square](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Manhattan Times Square Manhattan Save 100% on your flight $764 per person May 14 - May 17 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,348 reviews) Everything was ok. Nothing special Reviewed on Feb 24, 2026 Don't see what you're looking for? See all available trips from Columbus to Ossining [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-25/2026-04-01/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=LGA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](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=PKG_SPRING_PROMO_6190653) ### Discover the most popular places to visit in Ossining ![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) #### 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.com/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.com/Thomas-J-Watson-Research-Center-Ossining.d6087173.Vacation-Attraction) ## Ossining Hotel Deals ![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 Fully refundableReserve now, pay when you stay $172 nightly $191 total Mar 1 - Mar 2 Total with taxes and fees 8.4/10 Very Good! (115 reviews) Room was clean and hotel has wonderful amenities and nice people! Nelson and Marco were amazing! Will stay again Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%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 Fully refundableReserve now, pay when you stay $135 nightly $155 total Mar 4 - Mar 5 Total with taxes and fees 8.2/10 Very Good! (1,576 reviews) Very noisy this time. I normally enjoy it there. Teens and young kids all down the hallway running and making noise all night until early morning. This made my stay very uncomfortable. Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=438&PinnedHotelID=438&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 Fully refundableReserve now, pay when you stay $106 nightly $123 total Mar 22 - Mar 23 Total with taxes and fees 9/10 Wonderful! (1,079 reviews) We ordered from Expedia 2 nights, with breakfast Reviewed on Feb 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F22%2F2026&endDate=3%2F23%2F2026&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6190653) [See all 1,323 properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F26%2F2026&endDate=2%2F27%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. ## Find the Best Ossining Vacation Packages ## Ossining Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Closest Airport | LaGuardia Airport (LGA) | | Population | 25,400 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Franklin D. Roosevelt State Park](https://www.expedia.com/Franklin-D-Roosevelt-State-Park-Yorktown-Heights.d553248621561873121.Vacation-Attraction), [Paramount Hudson Valley Theater](https://www.expedia.com/Paramount-Hudson-Valley-Theater-Peekskill.d6131861.Vacation-Attraction) and [Rockefeller Archive Center](https://www.expedia.com/Rockefeller-Archive-Center-Tarrytown.d6211043.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) 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Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does an Ossining vacation package cost? ### What are the cheapest months to go to Ossining? ### How many days is enough for Ossining? ### Is it worth booking a vacation package to Ossining? ### How to find the best Ossining package deals? ### Is it cheaper to book an Ossining vacation as a package? ### When to book a vacation package to Ossining? ### Does Expedia offer Book Now, Pay Later Ossining vacation packages? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [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) - [Hotels near Sing Sing Correctional Facility 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Briarcliff Manor ](https://www.expedia.com/Things-To-Do-In-Briarcliff-Manor.d7040.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.