Ossining Holiday Rentals

We compare holiday rentals from owners across Booking.com, Vrbo and Expedia.

Destination
Dates
Guests
Search
  • Up-front pricing
  • No markup
  • Trusted partners

Compare Holiday Rentals, Villas & Resorts in Ossining

37 villas and rentals
Sort by
See More Properties

About Casai's Private Villas and Holiday Rentals in Ossining

Discover more than 37 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 443.11 ft², with nightly prices averaging £418.

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.

Other Places to Stay in Ossining, NY


Maryknoll 69 Properties
Hudson Hills Golf Course 66 Properties
Kitchawan Preserve 64 Properties
Thomas J. Watson Research Center 62 Properties
Crotonville 53 Properties
Ossining Historical Society 27 Properties
Louis Engel Waterfront Park 27 Properties
Merchants Square 25 Properties
Pleasant Square 25 Properties
Sing Sing Prison Museum 25 Properties
Snowden Avenue Park 25 Properties
Depot Square 25 Properties

There are 37 Ossining, NY Vacation Rentals

Recently Booked Hotels, Resorts, or Rentals in Ossining

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:

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

As of 2026, Casai boasts over 37 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.