Title: Ossining Vacation Packages 2026 from $480 | 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 $480 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## 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. ![Topping Rose House](https://images.trvl-media.com/lodging/6000000/5590000/5581400/5581380/8b4b1f10_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Topping Rose House $480 per person Mar 15 - Mar 18 found 21 hours ago Roundtrip flight included Dallas (DFW) to New York (JFK) 9.2/10 Wonderful! (136 reviews) Great rooms, staff and food Reviewed on Sep 28, 2025 ![Hotel St. James](https://images.trvl-media.com/lodging/2000000/1150000/1144500/1144474/ecd19bcc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel St. James Manhattan $601 per person Apr 14 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (6,546 reviews) Best location!!! Room itself was dated and small but it was clean and fine for our needs. Staff was helpful and allowed early check in for $25 and late checkout plus baggage holding. Reviewed on Feb 9, 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 $866 per person Apr 14 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,790 reviews) Great hotel, our room was warm and clean. The staff were very helpful and friendly. It was quite busy considering it was January but they were very organised. The breakfast selection was wonderful. Would recommend this hotel. Reviewed on Feb 8, 2026 ![NobleDEN Hotel](https://images.trvl-media.com/lodging/9000000/8690000/8682300/8682234/cb1dc844_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### NobleDEN Hotel Manhattan $904 per person Apr 14 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to New York (JFK) 9.8/10 Exceptional! (1,411 reviews) Super convenient hotel. Spotlessly clean. Lovely staff. Complimentary coffee / tea & amazing pastries from the beautiful bakery across the road. Reviewed on Feb 9, 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 $543 per person Apr 16 - Apr 19 found 1 day ago Roundtrip flight included Atlanta (ATL) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,348 reviews) Staff was lovely, rooms were clean and modern, location was excellent. I don’t believe the hype about breakfast though - you can get far better food elsewhere. Reviewed on Feb 9, 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/2026-03-10/2026-03-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=LGA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### 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 $179 nightly $199 total Feb 15 - Feb 16 Total with taxes and fees 8.2/10 Very Good! (109 reviews) Staff were very pleasant. Reviewed on Jan 26, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F15%2F2026&endDate=2%2F16%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 $124 nightly $142 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (1,527 reviews) Room was very clean and comfortable. Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%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 Fully refundableReserve now, pay when you stay $188 nightly $215 total Mar 9 - Mar 10 Total with taxes and fees 8.6/10 Excellent! (1,277 reviews) Checks all the boxes! Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F9%2F2026&endDate=3%2F10%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=6190653) [See all 1,335 properties in Ossining](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F11%2F2026&endDate=2%2F12%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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