Title: 20 Best B&B in Ossining, NY - Bed and Breakfast from $315 | 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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Feb 27 - Mar 1](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-02-27&endDate=2026-03-01&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Mar 6 - Mar 8](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-03-20&endDate=2026-03-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=6190653&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Ossining bed & breakfast ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/383d1993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/6c09864d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/126b99ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/ac02d781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cromwell Manor Inn [](https://www.expedia.com/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) Cornwall 9.4/10 Exceptional (95 reviews) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amrita $267 nightly $315 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/eb625d64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/a52a667e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Non Smoking (Deluxe Fireplace King) | Premium bedding, minibar, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/e2cd3114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/cd131fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Lane Inn [](https://www.expedia.com/Danbury-Hotels-West-Lane-Inn.h24290702.Hotel-Information) Ridgefield 9.8/10 Exceptional (54 reviews) "Lovely home, very friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia $344 nightly $395 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Danbury-Hotels-West-Lane-Inn.h24290702.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.com/Hotel-Search?startDate=2026-03-04&endDate=2026-03-05®ionId=6190653&adults=2&lodging=BED_AND_BREAKFAST&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.com/deals?rfrr=AA_SPRING_PROMO_6190653) ![](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%2FOssining-Bed-And-Breakfast.d6190653-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Bed-And-Breakfast.d6190653-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Ossining Hotel Reviews ![Windrose On Hudson](https://images.trvl-media.com/lodging/113000000/112810000/112806700/112806652/f251141f_y.jpg) ### Windrose On Hudson 10/10 Excellent "We loved it" [](https://expedia.com/Ossining-Hotels-Crotonville-Hotel.h112806652.Hotel-Information) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "yes" [](https://expedia.com/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Hotel NoMa, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/2000000/1090000/1088100/1088006/0bfe077b_y.jpg) ### Hotel NoMa, Trademark Collection by Wyndham 10/10 Excellent "Great " [](https://expedia.com/White-Plains-Hotels-Radisson-Hotel-New-Rochelle.h1088006.Hotel-Information) ![LIV Hotel Bronx](https://images.trvl-media.com/lodging/118000000/117970000/117967600/117967593/1c497b69_y.jpg) ### LIV Hotel Bronx 10/10 Excellent "I was extremely surprised by how comfortable clean and chill this place was other than the fact that the microwave is downstairs that’s OK. The ice machine is downstairs. That’s OK. There will be a refrigerator in your room and the rooms are clean and up-to-date. I love that I would totally stay here again. " [](https://expedia.com/New-York-Hotels-LIV-Hotel-Bronx.h117967593.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 "Everyone was super helpful!" [](https://expedia.com/White-Plains-Hotels-Hampton-Inn-Suites-Yonkers.h2647825.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 "Room was clean" [](https://expedia.com/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 "It was simple nothing to complain about but nothing special" [](https://expedia.com/Nyack-Hotels-DoubleTree-By-Hilton-Hotel-Nanuet.h736.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 excellent service in the restaurant was very good front desk hospitality very good .had eonerful stay at the westchester marriott.i will return" [](https://expedia.com/Tarrytown-Hotels-Westchester-Marriott.h10829.Hotel-Information) ![Ramada by Wyndham Bronx](https://images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg) ### Ramada by Wyndham Bronx 10/10 Excellent "Great place! " [](https://expedia.com/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.Hotel-Information) ## Find out more about Ossining ## Ossining B&B information | Number of reviews | 149 | | ----------------- | ------ | | Accommodation | 10 B&B | | Lowest Price | $315 | | Highest Price | $395 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Ossining? ### What is the difference between a Ossining Bed & Breakfast and a hotel? ## 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) - [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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[Dallas to Croton-on-Hudson ](https://www.expedia.com/lp/flights/178253/183658/dallas-to-croton-on-hudson) - [Sing Sing Prison Museum ](https://www.expedia.com/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction) - [Snowden Avenue Park ](https://www.expedia.com/Snowden-Avenue-Park-Ossining.d553248621558038861.Vacation-Attraction) - [Depot Square ](https://www.expedia.com/Depot-Square-Ossining.d553248621558038859.Vacation-Attraction) - [Sing Sing Correctional Facility ](https://www.expedia.com/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction) - [Nelson Park ](https://www.expedia.com/Nelson-Park-Ossining.d553248621557931331.Vacation-Attraction) - [Louis Engel Waterfront Park ](https://www.expedia.com/Louis-Engel-Waterfront-Park-Ossining.d553248621587293691.Vacation-Attraction) - [Visit Maryknoll ](https://www.expedia.com/Maryknoll.dx3000449058) - [Visit Briarcliff Manor ](https://www.expedia.com/Briarcliff-Manor.dx7040) - [Croton Point Park ](https://www.expedia.com/Croton-Point-Park-Croton-on-Hudson.d6093731.Vacation-Attraction) - [Van Cortlandt Manor ](https://www.expedia.com/Van-Cortlandt-Manor-Croton-on-Hudson.d6207691.Vacation-Attraction) - [Corning Tower ](https://www.expedia.com/Corning-Tower-Croton-on-Hudson.d553248621532664094.Vacation-Attraction) - [Hardscrabble Wilderness Area ](https://www.expedia.com/Hardscrabble-Wilderness-Area-Briarcliff-Manor.d553248621587293678.Vacation-Attraction) - [Rockland Lake State Park Championship Golf Course ](https://www.expedia.com/Rockland-Lake-State-Park-Championship-Golf-Course-Congers.d6253469.Vacation-Attraction) - [Visit Croton-on-Hudson ](https://www.expedia.com/Croton-On-Hudson.dx183658) - [Croton Landing Park ](https://www.expedia.com/Croton-Landing-Park-Croton-on-Hudson.d553248621587293679.Vacation-Attraction) - [Where to stay in Croton-on-Hudson ](https://www.expedia.com/Croton-On-Hudson.dx183658.Where-To-Stay) - [Car rentals near Ossining Historical Society ](https://www.expedia.com/Car-Rentals-In-Ossining-Historical-Society.d6207717.Car-Rental-Guide) - [Car rentals near Crotonville ](https://www.expedia.com/Car-Rentals-In-Crotonville.d553248635975868892.Car-Rental-Guide) - 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