Title: Ossining Vacation Packages & Trips 2026 from CA $585 | 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) ![](https://images.trvl-media.com/place/6190653/d6b06ec0-5d8e-4f01-b77d-2dc521a46ea1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Ossining Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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.ca/Tarrytown-Music-Hall-Tarrytown.d6211022.Vacation-Attraction), [Van Cortlandt Manor](https://www.expedia.ca/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) and [Sing Sing Correctional Facility](https://www.expedia.ca/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. ## Top Ossining Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 CA $585 per person Apr 25 - Apr 27 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (6,546 reviews) Clean room safe location Reviewed on Feb 8, 2026 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/922bba74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,410 per person Mar 14 - Mar 21 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,678 reviews) Hip boutique hotel with an industrial cozy vibe. Rooms are sumple but have everything you need. The libby bar and cafe are nice. Attached to Serafina restaurant. Great lication overall and parking across the street. Reviewed on Feb 6, 2026 ![Omni Berkshire Place](https://images.trvl-media.com/lodging/1000000/30000/23600/23597/181afb96_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Berkshire Place Manhattan CA $1,829 per person Mar 21 - Mar 28 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,042 reviews) We had a great stay, and it was an excellent location! The restaurant was also fabulous! Reviewed on Jan 22, 2026 ![Hotel 57](https://images.trvl-media.com/lodging/2000000/1210000/1208300/1208242/954f5b6b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel 57 Manhattan CA $786 per person Mar 11 - Mar 16 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.2/10 Very Good! (1,287 reviews) the room was cold. Everything else was ok. Nothing spectacular. Good place to stay for a day or two. Reviewed on Feb 6, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/7801a5d8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $1,197 per person Mar 13 - Mar 15 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,000 reviews) The entire stay was exceptional! From the point of entry to departure 10/10 Reviewed on Jan 29, 2026 ## Ready to book your vacation to Ossining? Choose your dates ## 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 CA $220 CA $246 total Feb 15 - Feb 16 includes taxes & fees 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) ![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 CA $214 CA $291 total Mar 9 - Mar 10 includes taxes & fees 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=09%2F03%2F2026&endDate=10%2F03%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 Fully refundableReserve now, pay when you stay CA $139 CA $162 total Feb 22 - Feb 23 includes taxes & fees 8.8/10 Excellent! (1,058 reviews) Thank you to the staff at DoubleTree in Nanuet, NY. Excellent service Clean rooms Respectful staff Great breakfast. Thank you again… 😊 Reviewed on Feb 3, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=736&PinnedHotelID=736&HadPinnedHotel=true®ionId=6190653) [See all 1,326 properties in Ossining](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&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. ![](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.ca/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.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](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. Scan the QR code with your device camera and download our app