58+ Private Villas and Holiday Rentals in Ossining |
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Ossining Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Ossining

Discover more than 58 vacation rentals available in Ossining. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Ossining.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Ossining, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Ossining. On average, places to stay near Ossining offer 1181.96 ft², with nightly prices averaging US $623.

With Casai, finding and comparing holiday rentals in Ossining is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Ossining

Type Count
Vacation Homes 34
Holiday Apartments 9
Cottages 5
Villas 1

Use these Quick Filters to Find a Holiday Rental in Ossining

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal 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

Casai 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 holiday rentals in Ossining?

With numerous options available in Ossining, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Ossining:

Which holiday homes in Ossining are best for families?

If you're searching for a family-friendly holiday home in Ossining, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Ossining:

How many Casai.com holiday rentals are available in Ossining?

As of 2025, Casai boasts over 58 properties listed in the Ossining area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Ossining.


People Also Ask

There are 58 Ossining, NY Holiday Rentals

Recently Booked Holiday Rentals in Ossining