Title: 5 Stars Hotels in Ossining, New York from CA $235 - Find Cheap Ossining Hotels With 5 Stars | Expedia.ca [Ossining Travel Guide](https://expedia.ca/Ossining.dx6190653)[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) ![#BeachBound After a long day at the beach, nothing beats a relaxing sunset at the dock.](https://images.trvl-media.com/place/6190653/b605ff9b-378c-42c4-a0b1-690b04a1daa9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by regina palmieri # 5 Stars Hotels in Ossining, New York from CA $235 - ![](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 5 Star Hotels Tonight [Jan 5 - Jan 6](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-05&endDate=2026-01-06&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 6 - Jan 7](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-06&endDate=2026-01-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-09&endDate=2026-01-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-16&endDate=2026-01-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining 5-star hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/80a97b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/w4000h2662x0y0-aae7375c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/45a95d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, steam room, body treatments, hydrotherapy, hot stone massages](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/daf1d0e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Opus Westchester, Autograph Collection [](https://www.expedia.ca/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) White Plains 9.2/10 Wonderful (529) "our room was very clean on beds very comfortable staff friendly, breakfast wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan CA $438 CA $548 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Ossining-Hotels.s50-0-d6190653.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Ossining-Hotels.s50-0-d6190653.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Ossining. ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta White Plains Downtown 66 Hale Ave White Plains NY CA $218 CA $295 total Feb 1 - Feb 2 includes taxes & fees 8.6/10 Excellent! (1,197 reviews) [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Greenwich 1800 E Putnam Avenue Old Greenwich CT CA $255 CA $294 total Jan 23 - Jan 24 includes taxes & fees 8.4/10 Very Good! (1,002 reviews) [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Hotel Zero Degrees Danbury](https://images.trvl-media.com/lodging/17000000/16270000/16263900/16263812/1fb60e7f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Zero Degrees Danbury 15 Milestone Road Danbury CT CA $204 CA $235 total Jan 8 - Jan 9 includes taxes & fees 9/10 Wonderful! (1,003 reviews) [](https://expedia.ca/Danbury-Hotels-Hotel-Zero-Degrees-Danbury.h16263812.Hotel-Information) Still don't see what you're looking for? [See all properties in Ossining.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=06%2F01%2F2026&endDate=07%2F01%2F2026®ionId=6190653&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Ossining Sing Sing Prison Museum offers a fascinating glimpse into America's most notorious correctional facility, with guided tours by former officers. Hike the scenic Old Croton Aqueduct Trail and then grab lunch at one of the diverse restaurants along the Hudson River waterfront. [See all hotels in Ossining](https://www.expedia.ca/Hotel-Search?startDate=2026-01-19&endDate=2026-01-20&adults=2®ionId=6190653) ![Main building at Maryknoll](https://images.trvl-media.com/place/3000449058/eaa5b59e-44e4-4686-a478-33459da1d8df.jpg?impolicy=fcrop&w=899&h=673&p=1&q=high) Photo by louann ohora ## Top Ossining Hotel Reviews ## Find out more about Ossining ## Five Star Hotels in Ossining There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Ossining so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Ossining and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Ossining Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Ossining The results are in, and Ossining 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Ossining! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Ossining today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Ossining? > - Search for the lowest price per night from CA $235 ### What makes a hotel 5 stars in Ossining? ### Are there any 5-star all-inclusive resorts in Ossining? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Upper Manhattan ](https://www.expedia.ca/1Star-Upper-Manhattan-New-York-Hotels.s10-n553248635074842933-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Central Park North ](https://www.expedia.ca/2Star-Central-Park-North-New-York-Hotels.s20-n553248635975749528-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Harriman ](https://www.expedia.ca/2Star-Harriman-Hotels.s20-0-d183682.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Manorhaven ](https://www.expedia.ca/2Star-Manorhaven-Hotels.s20-0-d553248634998695724.Travel-Guide-Filter-Hotels) - 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