Title: The Best 5 Star Hotels in Ossining, NY from $185 | Expedia.com [Ossining Travel Guide](https://expedia.com/Ossining.dx6190653)[Hotels in Ossining](https://expedia.com/Ossining-Hotels.d6190653.Travel-Guide-Hotels)[Vacation Rentals in Ossining](https://expedia.com/Ossining-Vacation-Rentals.d6190653.Travel-Guide-VacationRentals)[Flights to Ossining](https://expedia.com/Cheap-Flights-To-Ossining.d6190653.Travel-Guide-Flights)[Car Rentals in Ossining](https://expedia.com/Car-Rentals-In-Ossining.d6190653.Car-Rental-Guide)[Ossining Vacation Packages](https://expedia.com/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__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](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 [Feb 6 - Feb 7](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-07&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-13&endDate=2026-02-15&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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/766b0b9d.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) ![Egyptian cotton sheets, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/2000000/1790000/1789400/1789323/1bd56ddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Opus Westchester, Autograph Collection [](https://www.expedia.com/White-Plains-Hotels-The-Opus-Westchester.h1789323.Hotel-Information) White Plains 9.2/10 Wonderful (537 reviews) "The staff and executive suite we’re perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) queen $349 nightly $399 total Feb 7 - Feb 8 Total with taxes and fees [](https://www.expedia.com/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.com/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.com/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 $183 nightly $209 total Feb 27 - Feb 28 Total with taxes and fees 8.6/10 Excellent! (1,260 reviews) [](https://expedia.com/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 $195 nightly $224 total Feb 26 - Feb 27 Total with taxes and fees 8.4/10 Very Good! (1,002 reviews) [](https://expedia.com/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 $161 nightly $185 total Feb 7 - Feb 8 Total with taxes and fees 9/10 Wonderful! (1,004 reviews) [](https://expedia.com/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.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=6190653&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=6190653&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=6190653&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=6190653&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%2F2026®ionId=6190653&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F7%2F2026&endDate=2%2F8%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.com/Hotel-Search?startDate=2026-02-20&endDate=2026-02-21&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 Why not request the best of accommodations during your excursion to Ossining? After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Ossining so popular in the last year. There's no reason to delay a getaway to Ossining any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Ossining and get ready to enjoy the getaway of a lifetime. What are you waiting for? ### Get a Great Deal on 5-Star Hotels in Ossining You'll have a wonderful time at one of these 5-star hotels. Exceptional customer care, luxurious bedding, and deeply relaxing spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You can also expect excellent customer service from these hotels, so get ready for a wonderful adventure. What creature comforts do you want in your lodging? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A body scrub that will leave you feeling like a million bucks? Butler services? Whatever it is your heart desires, you're bound to find it here. But you aren't going to spend your entire vacation in your room, of course. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Ossining are waiting for you to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs. ### Make Your Escape The results are in, and Ossining 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to plan your next great escape. Choose one of Expedia's Ossining 5-star hotels today and relax in luxe surroundings 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 $185 ### 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 Rentals - Other - [New York Hotels ](https://www.expedia.com/New-York-Hotels.d178293.Travel-Guide-Hotels) - [4 Star Hotels in Manhattan ](https://www.expedia.com/4Star-Manhattan-New-York-Hotels.s40-n129440-0.Travel-Guide-Filter-Hotels) - [Hotels near Sing Sing Prison Museum ](https://www.expedia.com/Sing-Sing-Prison-Museum-Hotels.0-l553248621561873062-0.Travel-Guide-Filter-Hotels) - [Hotels near Snowden Avenue Park ](https://www.expedia.com/Snowden-Avenue-Park-Hotels.0-l553248621558038861-0.Travel-Guide-Filter-Hotels) - [Hotels near Ossining Station ](https://www.expedia.com/Ossining-Station-Hotels.d6338907.Travel-Guide-Hotels) - 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