Title: Book the Best Ossining Hotels with FREE WIFI in 2026 | 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)[Ossining Vacation Packages](https://expedia.ca/Ossining.d6190653.Destination-Travel-Guides) ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by louann ohora ![](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Ossining Hotels with Wifi Tonight [Feb 24 - Feb 25](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-02-24&endDate=2026-02-25&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 25 - Feb 26](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-02-25&endDate=2026-02-26&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 27 - Mar 1](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-02-27&endDate=2026-03-01&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-03-06&endDate=2026-03-08&adults=2&amenities=WIFI&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining hotels with wifi ![Restaurant](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/d1beb6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/589f9bbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/30d2fd7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/1b1bee23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Windrose On Hudson [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) Ossining 8.2/10 Very good (114 reviews) "Great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy [](https://www.expedia.ca/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![Outdoor banquet area](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/05588dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/0ca0a1f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/51ae2321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/102000000/101860000/101852400/101852343/6407ae3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Castle Retreat w/ Pool, BBQ, Game Room & Pets OK! [](https://www.expedia.ca/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) Ossining 9.2/10 Wonderful (7 reviews) "Communication was excellent. The house itself is older and fine for its age, but " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan O. CA $653 CA $1,331 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Ossining-Hotels-Castle-Retreat-W-Pool.h101852343.Hotel-Information) ![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/6e503ed4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/w3000h1944x0y0-bf620bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/ae91b214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa](https://images.trvl-media.com/lodging/122000000/121530000/121520500/121520491/11e211e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW 45 Wolden Rd Ossining NY 10562 [](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) Ossining CA $503 CA $1,234 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Ossining-Hotels-Foliage-At-Westchester-Manor-Near-Sleepy-Hollow.h121520491.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/c8911274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/e7b14123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/e72867a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182497/dbeddb50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1BR Queen near NYC | Trails, Biking & Sauna Bliss [](https://www.expedia.ca/Ossining-Hotels-1BR-Queen-Near-NYC-Trails.h121182497.Hotel-Information) Ossining CA $392 CA $498 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Ossining-Hotels-1BR-Queen-Near-NYC-Trails.h121182497.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/d63a6691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, foosball, offices](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/b1ec5991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/60fba9ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121190000/121182500/121182499/7a4af8d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Near NYC! | Stylish Guestroom [](https://www.expedia.ca/Ossining-Hotels-Near-NYC-Stylish-Guestroom.h121182499.Hotel-Information) Ossining CA $392 CA $498 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Ossining-Hotels-Near-NYC-Stylish-Guestroom.h121182499.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/5a24bb82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/ea876890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/49a9e13e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121190000/121182600/121182502/f51e4cd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Polished 1BR w/ Accessible Room Features + Sauna [](https://www.expedia.ca/Ossining-Hotels-Polished-1BR-W-Accessible-Room-Features-Sauna.h121182502.Hotel-Information) Ossining 6.0/10 (1 review) "We could not find location in dark and rain. Only given GPS info and no name of hotel or property. Once we arrived guard at guardhouse could not assist as we could not affirm name. When finally able to track down contact info for the vacation property company that listed the rental they had to share hotel front desk info and that’s when we learned name was Windrose On Hudson. Very stressful situation- enjoyed historical location. Great facility, not so great TV/streaming set-up… cable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nada S. CA $392 CA $500 total includes taxes & fees Mar 1 - Mar 2 [](https://www.expedia.ca/Ossining-Hotels-Polished-1BR-W-Accessible-Room-Features-Sauna.h121182502.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/ef0e434d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/f1250e4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/61ef7140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/e714a3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### LIV Hotel Bronx - Newly Built [](https://www.expedia.ca/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information) Bronx 7.2/10 Good (457 reviews) "Our stay was awesome, clean, cozy and we slept well." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hidelisa CA $159 CA $187 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/New-York-Hotels-LIV-Hotel-Bronx.h117967593.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/76122822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/a57d093b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Land view from property](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/407ec306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/10000000/9500000/9498900/9498859/cf8502df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Heidi's Inn [](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) Brewster 8.8/10 Excellent (822 reviews) "Clean room with very friendly and helpfull staff with a light breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $177 CA $192 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Poughkeepsie-Hotels-Heidis-Inn-Brewster-New-York.h9498859.Hotel-Information) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/b0b0d087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/020e6ad2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/ff2ecf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/700000/690800/690766/cc0a2b26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Danbury - I-84 by IHG [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) Danbury 9.2/10 Wonderful (329 reviews) "We enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne CA $169 CA $194 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Danbury-Hotels-Holiday-Inn-Express-Hotel-Suites-Danbury-I-84.h690766.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/30239db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/3a1a9879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/80e487b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, bed sheets](https://images.trvl-media.com/lodging/37000000/36490000/36486800/36486712/6806b0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Brewster [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information) Brewster 9.0/10 Wonderful (546 reviews) "Always great service and clean, comfy rooms. Breakfast is also decent every time, which isn’t always the case at hotels " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jared CA $173 CA $188 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Poughkeepsie-Hotels-Comfort-Inn.h36486712.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-10&endDate=2026-03-11®ionId=6190653&adults=2&amenities=WIFI&sort=RECOMMENDED&openPlayBack=true) ![](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=AFFINITY_SPRING_PROMO_6190653) ## Top Ossining Hotel Reviews ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "Staff is great, rooms very clean I really enjoyed our stay " [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Hampton Inn & Suites Yonkers](https://images.trvl-media.com/lodging/3000000/2650000/2647900/2647825/e36e4673_y.jpg) ### Hampton Inn & Suites Yonkers 10/10 Excellent "Awesome " [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.Hotel-Information) ![Westchester Marriott](https://images.trvl-media.com/lodging/1000000/20000/10900/10829/w3995h2667x0y0-3f6e8d0f_y.jpg) ### Westchester Marriott 10/10 Excellent "Room was big and clean. The staff was great and very helpful. " [](https://expedia.ca/Tarrytown-Hotels-Westchester-Marriott.h10829.Hotel-Information) ![Hampton Inn & Suites Yonkers - Westchester](https://images.trvl-media.com/lodging/16000000/15740000/15731000/15730982/2770772f_y.jpg) ### Hampton Inn & Suites Yonkers - Westchester 10/10 Excellent "Yes, excellent accommodation" [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers-Westchester.h15730982.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Yes" [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Sonesta Simply Suites Nanuet](https://images.trvl-media.com/lodging/1000000/700000/694300/694250/a9ba8283_y.jpg) ### Sonesta Simply Suites Nanuet 10/10 Excellent "This was a good trip and the accommodations were really appreciated good place to stay at" [](https://expedia.ca/Nyack-Hotels-Sonesta-Simply-Suites-Nanuet.h694250.Hotel-Information) ![Ardsley Acres Hotel Westchester](https://images.trvl-media.com/lodging/2000000/1170000/1166900/1166864/4b305bf7_y.jpg) ### Ardsley Acres Hotel Westchester 10/10 Excellent "Good " [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](https://images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "Clean" [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ![DoubleTree by Hilton Hotel Nanuet](https://images.trvl-media.com/lodging/1000000/10000/800/736/w3839h2556x0y3-9a7a26d9_y.jpg) ### DoubleTree by Hilton Hotel Nanuet 10/10 Excellent "The room was clean and the staff people were friendly and helpful. Parking was okay. our room was down a long wing to get to, but we parked near the entrance near our room and is was right there." 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