Title: Ossining Villas from CA $1,266 | 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) ![](https://mediaim.expedia.com/destination/2/71c4a83d479d9d5736259a6b7bd056c1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Linda Zanetti # Search Ossining Villa Rentals from CA $1,266 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-17&endDate=2025-10-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-11-07&endDate=2025-11-09&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Ossining Villas ![Terrace/patio](https://images.trvl-media.com/lodging/80000000/79910000/79908200/79908172/864c5b00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/80000000/79910000/79908200/79908172/197c7b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/80000000/79910000/79908200/79908172/6b47161b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/80000000/79910000/79908200/79908172/29572562.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery Woodbury 10/10 Exceptional (27) "Truly gorgeous house and surroundings! The owner has thought of everything and created a wonderful retreat. We were a total of 9 adults representing 3 generations and we had space and activities for everyone. Great location as well!" CA $945 CA $2,006 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Highland-Mills-Hotels-Kick-Back-Relax-In-This-Peaceful.h79908172.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/9959c91a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/ebcfc23f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/cb7ba131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119730000/119724400/119724381/e918daaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 7 BR Mansion , Celebration Welcomes Norwalk 10/10 Exceptional (1) "I had a wonderful stay at this house. It was very clean, comfortable, and beautifully maintained.Everything was exactly as described, and I really appreciated the welcoming atmosphere. Even though I only stayed for one day, it was an amazing experience. I would definitely recommend this place and would love to stay again in the future." CA $840 CA $1,266 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Norwalk-Hotels-Spacious-7-Bedroom-House-In-Delightful-Norwalk-With-AC.h119724381.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/abd47b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/31f65901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/77444f8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![11 bedrooms, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/fca95a12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Upstate Historical Artist Villa w/ firepit, pool and close to Candlewood Lake CT Brewster 9.2/10 Wonderful (7) "Property was exactly what we were looking for with a group as large as ours (14 people). Plenty of indoor and outdoor space. Great kitchen as well (cooked all of our meals in the house for the whole group)." CA $1,191 CA $2,192 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Brewster-Hotels-Upstate-Historical-Artist-Villa-W-Firepit.h101878310.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=2025-10-26&endDate=2025-10-27®ionId=6190653&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](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-Villas.d6190653-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOssining-Villas.d6190653-aaVillas.Travel-Guide-Accommodation) ## Top Ossining Hotel Reviews ![Ramada by Wyndham Bronx](//images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg) ### Ramada by Wyndham Bronx 10/10 Excellent "Good place" [](https://expedia.ca/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Stamford / New York City](//images.trvl-media.com/lodging/1000000/30000/25000/24963/af81668d_y.jpg) ### La Quinta Inn & Suites by Wyndham Stamford / New York City 10/10 Excellent "Yes" [](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information) ![DoubleTree by Hilton Stamford](//images.trvl-media.com/lodging/1000000/10000/5300/5292/f2f8be91_y.jpg) ### DoubleTree by Hilton Stamford 10/10 Excellent "Clean room, attetive staff, clise to Metro North, business friendly, quiet, great experience" [](https://expedia.ca/Stamford-Hotels-Hilton-Stamford-Hotel-Executive-Meeting-Center.h5292.Hotel-Information) ![The Armon Stamford Hotel & Conference](//images.trvl-media.com/lodging/90000000/89820000/89818900/89818854/99ae042b_y.jpg) ### The Armon Stamford Hotel & Conference 10/10 Excellent "It was soooo clean " [](https://expedia.ca/Stamford-Hotels-The-Armon-Hotel-Conference.h89818854.Hotel-Information) ![Best Western Paramus Hotel & Suites](//images.trvl-media.com/lodging/1000000/870000/869100/869030/8ee68b48_y.jpg) ### Best Western Paramus Hotel & Suites 10/10 Excellent "Just a quick overnight for a wedding, but check-in was easy, room was clean and comfortable, and surprisingly hotel was very quiet during our stay. Exactly what we needed for a quick stay." [](https://expedia.ca/Paramus-Hotels-Best-Western-Paramus-Hotel-Suites.h869030.Hotel-Information) ![Hampton Inn White Plains/Tarrytown](//images.trvl-media.com/lodging/1000000/30000/23300/23291/d5b0e16e_y.jpg) ### Hampton Inn White Plains/Tarrytown 10/10 Excellent "Normal" [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Armoni Inn & Suites](//images.trvl-media.com/lodging/1000000/20000/12100/12036/5f0c23aa_y.jpg) ### Armoni Inn & Suites 10/10 Excellent "We had an overnight stay; for this purpose, it was perfect." [](https://expedia.ca/Orangeburg-Hotels-Armoni-Inn-Suites.h12036.Hotel-Information) ![Royal Regency Hotel](//images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "Affordable and a pleasant stay. Hope you like purple." [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Baymont by Wyndham White Plains - Elmsford](//images.trvl-media.com/lodging/1000000/10000/500/438/w8985h6000x10y0-9d556f34_y.jpg) ### Baymont by Wyndham White Plains - Elmsford 10/10 Excellent "I have stayed here many times It is central to everything Clean ,pleasant ,efficient and professional On this particular stay the night desk clerk and the housekeeping staff were extremely helpful and nice " [](https://expedia.ca/White-Plains-Hotels-La-Quinta-Inn-Suites-By-Wyndham-White-Plains-Elmsford.h438.Hotel-Information) ## Find out more about Ossining ## Ossining Villas information | Number of reviews | 34 | | --- | --- | | Accommodation | 10 Villas | | Lowest Price | CA $1,266 | | Highest Price | CA $2,192 | ## Frequently asked questions ### Why book your villa in Ossining with Expedia? > We think vacation time shouldn't be difficult, so if you're looking for villas at an affordable price, Expedia can help. Stick to the budget and opt for an all-inclusive stay, or splurge on a high-end villa to spoil your nearest and dearest. Our search filters make it simple to find a retreat in Ossining that suits you best. ### How can I find cheap villas in Ossining? > With Expedia's helpful filter tool, reserving cheap villas in Ossining couldn't be easier. To find accommodations that'll make your wallet happy, narrow your search by amenities, star rating and budget. ### What is there to do near my villa in Ossining? > You'll find loads of awesome things to do and see in Ossining. Explore top attractions like [Sing Sing Correctional Facility](https://www.expedia.ca/Sing-Sing-Correctional-Facility-Ossining.d553248621558038857.Vacation-Attraction), [Thomas J. Watson Research Center](https://www.expedia.ca/Thomas-J-Watson-Research-Center-Ossining.d6087173.Vacation-Attraction) and [Louis Engel Waterfront Park](https://www.expedia.ca/Louis-Engel-Waterfront-Park-Ossining.d553248621587293691.Vacation-Attraction). [Ossining Historical Society](https://www.expedia.ca/Ossining-Historical-Society-Ossining.d6207717.Vacation-Attraction), [Sing Sing Prison Museum](https://www.expedia.ca/Sing-Sing-Prison-Museum-Ossining.d553248621561873062.Vacation-Attraction) and [Teatown Lake Reservation](https://www.expedia.ca/Teatown-Lake-Reservation-Ossining.d553248621560458588.Vacation-Attraction) also lure many visitors. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Briarcliff Manor](https://www.expedia.ca/4Star-Briarcliff-Manor-Hotels.s40-0-d7040.Travel-Guide-Filter-Hotels) - [Aparthotels in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Apart-Hotels.d7040-aaApartHotels.Travel-Guide-Accommodation) - [Condo Rentals in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Condos.d7040-aaCondos.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Briarcliff Manor](https://www.expedia.ca/Briarcliff-Manor-Hotels-Beach-Hotel.0-0-d7040-tBeachHotel.Travel-Guide-Filter-Hotels) - 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