Title: Ossining Villas from CA $2,209 | 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 $2,209 ![](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 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-10-31&endDate=2025-11-02&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [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 one month [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-11-21&endDate=2025-11-23&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6190653&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Ossining Villas ![Exterior](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/abd47b85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101880000/101878400/101878310/w1896h1262x4y4-cfbd0bcf.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) ![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) ### 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)." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eric L. CA $1,189 CA $2,209 total includes taxes & fees Nov 3 - Nov 4 [](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=2025-11-07&endDate=2025-11-08®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 ![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 "Liked the location. Needs updating, which you are now doing." [](https://expedia.ca/Stamford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Stamford-New-York-City.h24963.Hotel-Information) ![Hyatt Place New York/Yonkers](//images.trvl-media.com/lodging/11000000/10240000/10232200/10232108/w3837h2558x3y3-6fc198b6_y.jpg) ### Hyatt Place New York/Yonkers 10/10 Excellent "Very nice room. Very polite, efficient desk and breakfast personnel. Adequate parking. Good internet. All-in-all, a very nice place." [](https://expedia.ca/White-Plains-Hotels-Hyatt-Place-New-YorkYonkers.h10232108.Hotel-Information) ![Ramada by Wyndham Bronx](//images.trvl-media.com/lodging/1000000/470000/462500/462463/c9951f9d_y.jpg) ### Ramada by Wyndham Bronx 10/10 Excellent "The room was very clean, the staff was pleasant and respectful. Loved how quiet it was and the convenience to dining and entertainment. " [](https://expedia.ca/New-York-Hotels-Ramada-By-Wyndham-Bronx.h462463.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 "Great staff! Clean! Will stay again!" [](https://expedia.ca/Paramus-Hotels-Best-Western-Paramus-Hotel-Suites.h869030.Hotel-Information) ![Amsterdam Hotel](//images.trvl-media.com/lodging/1000000/30000/20800/20793/f5bb9592_y.jpg) ### Amsterdam Hotel 10/10 Excellent "Very clean hotel for a quick stay." [](https://expedia.ca/Stamford-Hotels-Amsterdam-Hotel.h20793.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 "This hotel was nice but it needs to be updated.... front desk was very pleasant and hospitable.. the breakfast was so so.. the turkey sausage was burnt. Everything else was fine.. dark roast coffee was delicious!" [](https://expedia.ca/White-Plains-Hotels-Hampton-Inn-White-Plains.h23291.Hotel-Information) ![Hilltop Inn & Suites](//images.trvl-media.com/lodging/112000000/111920000/111917200/111917184/56fb0262_y.jpg) ### Hilltop Inn & Suites 10/10 Excellent "The front desk staff was very helpful and friendly!" [](https://expedia.ca/Yonkers-Hotels-Hilltop-Inn-Suites.h111917184.Hotel-Information) ![Royal Regency Hotel](//images.trvl-media.com/lodging/1000000/50000/40900/40814/c5903df6_y.jpg) ### Royal Regency Hotel 10/10 Excellent "Staff very courteous!" [](https://expedia.ca/White-Plains-Hotels-Royal-Regency-Hotel.h40814.Hotel-Information) ![Hyatt Regency Greenwich](//images.trvl-media.com/lodging/1000000/20000/18200/18180/19d28016_y.jpg) ### Hyatt Regency Greenwich 10/10 Excellent "All good." [](https://expedia.ca/Stamford-Hotels-Hyatt-Regency-Greenwich.h18180.Hotel-Information) ## Find out more about Ossining ## Ossining Villas information | Number of reviews | 6 | | --- | --- | | Accommodation | 10 Villas | | Lowest Price | CA $2,209 | | Highest Price | CA $2,209 | ## 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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[Car rental Briarcliff Manor](https://www.expedia.ca/Car-Rentals-In-Briarcliff-Manor.d7040.Car-Rental-Guide) - [Car rental Croton-on-Hudson](https://www.expedia.ca/Car-Rentals-In-Croton-On-Hudson.d183658.Car-Rental-Guide) - [Car rental Pleasantville](https://www.expedia.ca/Car-Rentals-In-Pleasantville.d9121.Car-Rental-Guide) - [Briarcliff Manor Vacation Rentals](https://www.expedia.ca/Briarcliff-Manor-Vacation-Rentals.d7040.Travel-Guide-VacationRentals) - [Croton-On-Hudson Vacation Rentals](https://www.expedia.ca/Croton-On-Hudson-Vacation-Rentals.d183658.Travel-Guide-VacationRentals) - [Things to do in Briarcliff Manor](https://www.expedia.ca/Things-To-Do-In-Briarcliff-Manor.d7040.Travel-Guide-Activities) - [Things to do in Croton-on-Hudson](https://www.expedia.ca/Things-To-Do-In-Croton-On-Hudson.d183658.Travel-Guide-Activities) - [Book Villas in Ossining on Expedia.com](https://www.expedia.com/Ossining-Villas.d6190653-aaVillas.Travel-Guide-Accommodation)