Title: Ossining B&B: Find the Best Bed and Breakfast from CA $383 | 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 # Find a Bed and Breakfast in Ossining from CA $383 - ![](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 prices for these dates Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Ossining B&B ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/fda4e0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/a124fb3e.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) ![Exterior](https://images.trvl-media.com/lodging/84000000/83830000/83825100/83825039/94f72b71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cromwell Manor Inn Cornwall 9.6/10 Exceptional (91) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amrita CA $324 CA $383 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Cornwall-Hotels-Cromwell-Manor-Inn.h83825039.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/cd131fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Suite, 2 Bedrooms, Non Smoking (Family Suite with Kitchenette)](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/01d1eb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/a49ee991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Single Room | Living area](https://images.trvl-media.com/lodging/25000000/24300000/24290800/24290702/f1ac6fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### West Lane Inn Ridgefield 9.8/10 Exceptional (54) "Lovely home, very friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alicia CA $524 CA $603 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-12-12&endDate=2025-12-13®ionId=6190653&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_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.ca/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.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Bed-And-Breakfast.d6190653-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Ossining Hotel Reviews ![Amsterdam Hotel](https://images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "No complaints whatsoever and will always return to this hotel whenever I come back!😊" [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.Hotel-Information) ![Royal Regency Hotel](https://images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "it was great" [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Tarrytown House Estate](https://images.trvl-media.com/lodging/1000000/50000/49700/49674/a89a02a1_y.jpg) ### Tarrytown House Estate 10/10 Excellent "Very appreciative of the complimentary EV charging. " [](https://expedia.ca/White-Plains-Hotels-Tarrytown-House-Estate-On-The-Hudson.h49674.Hotel-Information) ![Sonesta White Plains Downtown](https://images.trvl-media.com/lodging/1000000/10000/10000/9979/2c718cc1_y.jpg) ### Sonesta White Plains Downtown 10/10 Excellent "I’ve rarely encountered a hotel in the U.S. with such outstanding hospitality from the staff. The rooms were newly renovated, very clean, and overall it was an excellent hotel." [](https://expedia.ca/White-Plains-Hotels-Sonesta-White-Plains-Downtown.h9979.Hotel-Information) ![Sleepy Hollow Hotel](https://images.trvl-media.com/lodging/1000000/10000/4000/3956/ee0f5c7a_y.jpg) ### Sleepy Hollow Hotel 10/10 Excellent "excellent place " [](https://expedia.ca/White-Plains-Hotels-Sleepy-Hollow-Hotel-Conference-Center.h3956.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 "Super clean, easy check in, fridge and toiletries in room. " [](https://expedia.ca/White-Plains-Hotels-Ardsley-Acres-Hotel-Westchester.h1166864.Hotel-Information) ![DoubleTree by Hilton Stamford](https://images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 10/10 Excellent "I will absolutely stay here again. Everything was great!" [](https://expedia.ca/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.Hotel-Information) ![Hyatt Regency Greenwich](https://images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "Had a great check in experience!" [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ![Hyatt Place New York/Yonkers](https://images.trvl-media.com/lodging/11000000/10240000/10232200/10232108/w3837h2558x3y3-6fc198b6_y.jpg) ### Hyatt Place New York/Yonkers 10/10 Excellent "Friendly staff , convenient location. Only thing I wished that the rooms had a microwave. " [](https://expedia.ca/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information) ## Find out more about Ossining ## Ossining B&B information | Number of reviews | 145 | | --- | --- | | Accommodation | 10 B&B | | Lowest Price | CA $383 | | Highest Price | CA $603 | ## Frequently asked questions ### Searching for B&Bs in Ossining? > If you're looking for something a little more offbeat than your standard hotel, a bed and breakfast could be a great option for your trip. While you're here, you can get to know Ossining by exploring its natural beauty. Consider a stop by Teatown Lake Reservation and Kitchawan Preserve. ### How do you know if a B&B is the best choice for your stay? > With attentive service, opportunities to mingle with other guests, and top-rated breakfasts, B&Bs offer a unique setting. ### What are the best B&Bs in Ossining? > Below is a B&B in the area: [Stanton House Inn](https://www.expedia.ca/Stamford-Hotels-Stanton-House-Inn.h33140789.Hotel-Information): 20 rooms. 15.1 mi (24.3 km) from the downtown core. Enjoy the deli and outdoor pool. ### When should I book my B&B in Ossining? > When you're planning your escape to Ossining, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 34°F. Average annual precipitation for Ossining is 51 inches. ### What is there to do in Ossining? > Spend some time exploring Teatown Lake Reservation and Kitchawan Preserve if you're hoping to see some of the area's natural features. You might put Sing Sing Correctional Facility and Thomas J. Watson Research Center on your list if you want to see more of the area. ### How can I get to and around Ossining? > Planning your excursions in and around Ossining is easier with these transportation options. Fly into Westchester County Airport (HPN), which is located 10.5 mi (16.8 km) from the city center. Otherwise, look for flights into Teterboro, NJ (TEB), which is 23.9 mi (38.5 km) away. 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