Title: Ossining Vacation Packages & Trips 2026 from CA $1,234 | 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. ![Luxury 3BR Family Home Game Room Parking](https://images.trvl-media.com/lodging/125000000/124090000/124084400/124084363/2ea3fd3b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Luxury 3BR Family Home Game Room Parking Bryn Mawr CA $1,234 per person May 1 - May 7 found 1 day ago Roundtrip flight included Toronto (YYZ) to White Plains (HPN) 10/10 Exceptional! (1 review) Beautiful layout. Property had everything that was needed for an awesome stay. Reviewed on Feb 27, 2026 ![Modern Luxury Home w GameRoom & Parking](https://images.trvl-media.com/lodging/102000000/101330000/101326200/101326114/5bea3ddd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Modern Luxury Home w GameRoom & Parking Southeast Yonkers CA $2,032 per person May 30 - Jun 2 found 1 day ago Roundtrip flight included Toronto (YTO) to White Plains (HPN) 7.2/10 Good! (5 reviews) This was an excellent House My birthday weekend was amazing I totally would book again Reviewed on Mar 17, 2024 ![Arthouse Hotel New York City](https://images.trvl-media.com/lodging/1000000/20000/12200/12117/0e6cbb94_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arthouse Hotel New York City Manhattan CA $1,662 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,843 reviews) Wish there were fridges in all of the rooms. Front desk were super polite and helpful. Reviewed on Mar 25, 2026 ![Park Central Hotel New York](https://images.trvl-media.com/lodging/1000000/10000/4200/4164/cb48c512_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Central Hotel New York Manhattan CA $1,595 per person Jun 8 - Jun 14 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Newark Liberty Intl. Airport (EWR) 7.6/10 Good! (3,962 reviews) Can't understand the negative reviews. We had a lovely 5 nights here and ejoyed every minute. Location is really excellent . We honestly could not fault this hotel, it had everything we needed. We will be definitely going back. Reviewed on Mar 25, 2026 ![1 Hotel Brooklyn Bridge](https://images.trvl-media.com/lodging/16000000/15400000/15399700/15399642/b1e6b86c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel Brooklyn Bridge CA $3,045 per person May 14 - May 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Newark Liberty Intl. Airport (EWR) 8.8/10 Excellent! (1,000 reviews) Excellent staff, clean room, fantastic onsite restaurants. Reviewed on Mar 10, 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/d1beb6ce_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 $233 CA $259 total Apr 1 - Apr 2 includes taxes & fees 8.4/10 Very Good! (120 reviews) hotel grounds are great the rooms need an update the staff is great Margorie is a pleasure to be around the grab and go is great the gym great i did not eat there the restaurant was not open. I would go back even though it is a bit far from my office. they do clean the room every day which to me ... Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%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 $174 CA $199 total Apr 7 - Apr 8 includes taxes & fees 8.2/10 Very Good! (1,615 reviews) Nice hotel, big rooms, basic breakfast, wifi didn’t work properly. Reviewed on Mar 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=438&PinnedHotelID=438&HadPinnedHotel=true®ionId=6190653) ![LIV Hotel Bronx - Newly Built](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### LIV Hotel Bronx - Newly Built 3530 Webster Ave Bronx NY Fully refundableReserve now, pay when you stay CA $192 CA $225 total Mar 29 - Mar 30 includes taxes & fees 8.2/10 Very Good! (421 reviews) Too noisy Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=117967593&PinnedHotelID=117967593&HadPinnedHotel=true®ionId=6190653) [See all 1,352 properties in Ossining](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F03%2F2026&endDate=28%2F03%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