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Ossining Vacation Rentals & One Degree Stays Homes

About Ossining Vacation Rentals

There are more than 61 vacation rentals that are available in Ossining. These rentals, including vacation rentals, One Degree Stays Homes (ODSs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an ODS property in Ossining.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With OneDegreeStays Ossining, you have the flexibility of comparing different options of various deals with a single click. Looking for an ODS with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (ODSs), and other popular Airbnb-style properties in Ossining. Places to stay near Ossining are 1131.06 ft² on average, with prices averaging US $610 a night.

OneDegreeStays makes it easy and safe to find and compare vacation rentals in Ossining with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Ossining

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 5
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ossining

★ Pro Tip: OneDegreeStays makes it easy to compare the best listings on ODS homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between ODS homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Ossining.

Weather in Ossining, NY

View the weather forecast for Ossining before booking your Ossining Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Ossining, NY

OneDegreeStays offers a large selection of top attractions around Ossining. Research things to do on your vacation before you visit Ossining.


Sing Sing Correctional Facility
Thomas J. Watson Research Center
Sing Sing Prison Museum
Teatown Lake Reservation
Hudson Hills Golf Course
Ossining Historical Society
Nelson Park
Louis Engel Waterfront Park
Merchants Square
Pleasant Square
Snowden Avenue Park
Depot Square
Kitchawan Preserve
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Capitol Theatre
Campgaw Mountain Ski Area
Empire City Casino
Palisades Center

Other Places to Stay in Ossining, NY


Nelson Park 94 Properties
Sing Sing Correctional Facility 91 Properties
Louis Engel Waterfront Park 88 Properties
Depot Square 85 Properties
Pleasant Square 77 Properties
Sing Sing Prison Museum 77 Properties
Snowden Avenue Park 77 Properties
Merchants Square 76 Properties
Ossining Historical Society 56 Properties
Maryknoll 51 Properties
Hudson Hills Golf Course 47 Properties
Teatown Lake Reservation 46 Properties

Frequently Asked Questions About Ossining?

What are the top vacation rentals in Ossining?

There are a lot of options in Ossining. If you plan on staying in the Ossining area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ossining:

Which vacation homes in Ossining are best for families?

If you are looking for a family-friendly vacation home in Ossining, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ossining:

How many onedegreestays vacation rentals are available in Ossining?

Currently, the total number of properties listed by One Degree Stays in 2025 is over 61 in the Ossining area, and still counting. By aggregating listings from multiple websites, One Degree Stays offers an immense amount of choice of the best ODS properties in Ossining. 


People Also Ask

There are 61 Ossining, NY Vacation Rentals

Recently Booked Vacation Rentals in Ossining