Title: Ossining Vacation Packages & Trips 2026 from CA $1,131 | 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 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 CA $1,131 per person May 18 - May 21 found 1 day ago Roundtrip flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9.2/10 Wonderful! (3,348 reviews) Room and general cleanliness of the entire hotel was great. Staff really are lovely . Great location, rooms are perfect. Breakfast was fantastic and a really great start to the day . Reviewed on Feb 20, 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 CA $1,757 per person Mar 29 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (2,790 reviews) We were not able to dim the lights in the room. We were able to hear conversations from other rooms. The lights were too bright or off. The service was great but not happy with the room lights Reviewed on Feb 20, 2026 ![The Fifth Avenue Hotel](https://images.trvl-media.com/lodging/97000000/96480000/96472700/96472655/d0a5c1e1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Fifth Avenue Hotel Manhattan CA $1,978 per person May 18 - May 21 found 1 day ago Roundtrip flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 9.6/10 Exceptional! (159 reviews) Room size was perfect. All staff were kind and helpful. Will stay here again! Reviewed on Feb 18, 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 CA $2,250 per person Mar 29 - Apr 4 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 9/10 Wonderful! (1,002 reviews) Staff were very accomodating and looked after my family well during our stay. Nothing was too difficult for them. Reviewed on Jan 17, 2026 ![](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.ca/deals?rfrr=PKG_SPRING_PROMO_6190653) ## 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 $254 CA $283 total Mar 5 - Mar 6 includes taxes & fees 8.2/10 Very Good! (113 reviews) We loved it Reviewed on Feb 16, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%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 $172 CA $197 total Feb 22 - Feb 23 includes taxes & fees 8.2/10 Very Good! (1,570 reviews) Clean Reviewed on Feb 20, 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 Fully refundableReserve now, pay when you stay CA $231 CA $310 total Mar 23 - Mar 24 includes taxes & fees 8.6/10 Excellent! (1,302 reviews) Rooms were clean, great location near the mall, friendly staff and great accommodations. Our initial issues were resolved by staff, so no complaints. I would stay again. Reviewed on Feb 18, 2026 [](https://expedia.ca/Hotel-Search?startDate=23%2F03%2F2026&endDate=24%2F03%2F2026&selected=9979&PinnedHotelID=9979&HadPinnedHotel=true®ionId=6190653) [See all 1,324 properties in Ossining](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F02%2F2026&endDate=23%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