Title: Ossining Vacation Packages & Trips 2025/2026 from CA $601 | 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/6190653/9ea2ffd5-f98e-40ce-8c31-b0c6a6a646c1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Ossining Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Linda Zanetti - ## 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. ![INNSiDE by Meliá New York Nomad](https://images.trvl-media.com/lodging/13000000/12630000/12628000/12627948/24f1e817_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### INNSiDE by Meliá New York Nomad Manhattan CA $601 per person Jan 9 - Jan 12 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.2/10 Wonderful! (2,030 reviews) The staff were super welcoming, it was a large hotel room on the top floor. Would definitely stay here again! Reviewed on Oct 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-12/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12627948&paandie=true&dealMarker=uqEoPNC4Zf08AZzhJOA92hcAQAG53r04tGggQjxiRouHpFQGADk_7R8594oOXVX8) ![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 $1,319 per person Jan 9 - Jan 12 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 9.6/10 Exceptional! (151 reviews) A perfect place to stay!! Reviewed on Sep 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-12/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=96472655&paandie=true&dealMarker=uqEoPNC4Zf08AZzhJOA92g4gOTzF2YZe8n-O2tBEs2itEbuxLgfAdvKWrIu7pK7w) ![Fouquet's New York](https://images.trvl-media.com/lodging/89000000/88280000/88270900/88270883/aba7521d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Fouquet's New York Manhattan CA $1,384 per person Jan 9 - Jan 12 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (NYC) 9.8/10 Exceptional! (58 reviews) Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-12/?FromAirport=YTO&Destination=NYC&NumRoom=1&NumAdult=2&NumChild=0&hotelId=88270883&paandie=true&dealMarker=uqEoPNC4Zf08AZzhJOA92s1VJuEPOooPTELRl9eph3XQ9i_9tqqodrDIiR3bUWzc) ![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 $1,348 per person Jan 9 - Jan 12 found 1 day ago Roundtrip flight included Toronto (YTO) to New York (JFK) 8.8/10 Excellent! (1,012 reviews) Nice hotel , needs a bit of tender love and care ! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-09/2026-01-12/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15399642&paandie=true&dealMarker=uqEoPNC4Zf08AZzhJOA92g4gOTzF2YZe8n-O2tBEs2iL3BL1QSQ-49aw99nlbynv) ### Things to do near Ossining Ossining, New York, offers a delightful blend of outdoor and family-friendly activities, making it perfect for a city-themed vacation. Visitors can enjoy skiing and explore local shopping areas. Additionally, nearby Tarrytown is known for picturesque wedding venues, adding a romantic touch to your trip. With its scenic beauty and vibrant community, Ossining promises a memorable experience for all travellers. **Shopping** In Ossining, check out [Rockland Bakery](https://www.expedia.ca/Rockland-Bakery-Hotels.0-l553248621532664487-0.Travel-Guide-Filter-Hotels) for local treats, only 12.9km away. If you're up for a drive, visit [Westchester's Ridge Hill](https://www.expedia.ca/Westchesters-Ridge-Hill-Hotels.0-l553248621558114293-0.Travel-Guide-Filter-Hotels), 22.5km away, for a variety of shops and family-friendly vibes. For an extensive experience, the [Woodbury Common Premium Outlets](https://www.expedia.ca/Woodbury-Common-Premium-Outlets-Hotels.0-l6127054-0.Travel-Guide-Filter-Hotels) is 27.4km away. **Recreation** Experience the vibrant atmosphere at [Tarrytown Music Hall](https://www.expedia.ca/Tarrytown-Music-Hall-Hotels.0-l6211022-0.Travel-Guide-Filter-Hotels), where live performances uplift your spirit. For relaxation, visit [Hardscrabble Wilderness Area](https://www.expedia.ca/Hardscrabble-Wilderness-Area-Hotels.0-l553248621587293678-0.Travel-Guide-Filter-Hotels), a serene retreat perfect for nature walks. Enjoy the outdoors at [Rockland Lake State Park Championship Golf Course](https://www.expedia.ca/Rockland-Lake-State-Park-Championship-Golf-Course-Hotels.0-l6253469-0.Travel-Guide-Filter-Hotels), offering a refreshing blend of sport and scenic beauty. **Adventure** At [Palisades Climb Adventure](https://www.expedia.ca/Palisades-Climb-Adventure-Hotels.0-l553248621532664490-0.Travel-Guide-Filter-Hotels), experience the thrill of ziplining and navigating an exhilarating ropes course surrounded by nature, located 11.3km from Ossining. For karting enthusiasts, Grand Prix New York offers high-speed fun, just 12.9km away. Explore the scenic Orange Trailhead, a fantastic outdoor access point, also 11.3km from Ossining. **Nightlife** Experience the vibrant nightlife in Ossining by enjoying a show at the [Westchester Broadway Theatre](https://www.expedia.ca/Westchester-Broadway-Theatre-Hotels.0-l6183430-0.Travel-Guide-Filter-Hotels), just 11.3km away. For some fun, visit [Lucky Strike](https://www.expedia.ca/Lucky-Strike-Hotels.0-l553248621532664489-0.Travel-Guide-Filter-Hotels) ArcadeAdventureZone, also 11.3km away. If you're in the mood for a film, head to [Maritime IMAX](https://www.expedia.ca/Maritime-IMAX-Hotels.0-l6129064-0.Travel-Guide-Filter-Hotels), located 38.6km away for an entertaining evening. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Best time to go to Ossining The best time to visit Ossining is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 30.0°F (-1.1°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | February | 31.6°F (-0.2°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | | March | 38.8°F (3.8°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | April | 49.8°F (9.9°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 60.1°F (15.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 68.9°F (20.5°C) | Light Rain | Mostly Sunny | Average | Average | | July | 75.6°F (24.2°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 73.9°F (23.3°C) | Light Rain | Mostly Sunny | Average | Average | | September | 66.9°F (19.4°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 56.1°F (13.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 44.2°F (6.8°C) | Light Rain | Mostly Sunny | Average | Average | | December | 36.3°F (2.4°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly High | ### Booking tips and Expedia advantages for Ossining To save money during your visit to Ossining, consider travelling from January to March when hotel prices are lower. Book your accommodation about a month in advance for the best rates, with Sundays being the cheapest day to stay. Use Expedia to find last-minute deals and compare prices easily. You can also save by bundling your hotel with flights and activities. For public transport, take advantage of the local bus system to navigate the area affordably. Finally, explore free activities like parks and local events to make the most of your trip without overspending. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Ossining are January to March, where the prices are slightly lower. This is in comparison to September to October and December, where prices are slightly higher. - **The best time to book a hotel:** Book your hotel in Ossining about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Ossining is Sunday. The most expensive day to stay in Ossining is Saturday. - **Find cheap hotels on Expedia:** Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from the lowest to the highest, making it easy to find the most affordable accommodations first. Additionally, you have the option to refine your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking. - **Consider bundling your trip:** You can save money by combining your Ossining hotel reservation with your flights and activities through an Expedia package. ## 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 7.8/10 Good! (60 reviews) Great stay in Croton on Hudson Amazing stay at this well run newly minted Hotel - it's got great space to wander on the grounds, I would like to come again. The staff was super helpful and made our stay even more special. Reviewed on Oct 26, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=112806652&PinnedHotelID=112806652&HadPinnedHotel=true®ionId=6190653) [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=112806652&PinnedHotelID=112806652&HadPinnedHotel=true®ionId=6190653) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Stamford 1 First Stamford Pl, Stamford, CT Fully refundableReserve now, pay when you stay CA $194 CA $223 total Nov 24 - Nov 25 includes taxes & fees 7.2/10 Good! (1,012 reviews) Very accommodating, clean and modern Reviewed on Oct 24, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=5292&PinnedHotelID=5292&HadPinnedHotel=true®ionId=6190653) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Royal Regency Hotel 165 Tuckahoe Rd, Yonkers, NY Fully refundableReserve now, pay when you stay CA $139 CA $171 total Dec 1 - Dec 2 includes taxes & fees 8.2/10 Very Good! (2,335 reviews) I love this place. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=40814&PinnedHotelID=40814&HadPinnedHotel=true®ionId=6190653) [See all 1,260 properties in Ossining](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F11%2F2025&endDate=04%2F11%2F2025®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 ![QR code to download the app](data:image/png;base64,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)