Ossining Summer Rentals, Cottages & Cabins

Book a Place to Stay in Ossining for Your Summer Getaway

About Ossining Summer Rental on Casai.com

With 44 summer rental in or near Ossining? Look no further than Casai for your upcoming summer getaway. Whether you're traveling with family, friends, or a group, we offer a wide selection of holiday homes and villas designed for the perfect summer retreat.

Our holiday homes and villas in Ossining come with a range of top amenities, including private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, nearby parks, luxurious bedrooms, bathtubs, and pet-friendly environments.

Searching for a relaxing retreat in Ossining to make unforgettable summer memories? Casai has you covered with a variety of options, including unique condos, luxury resorts, bungalows, cozy cabins, RVs, and cottages in Ossining.

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Frequently Asked Questions About Ossining Luxury Rentals

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 Summer Rentals in Ossining:

In 2025, Casai offers 44 summer rentals in or around Ossining. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Ossining is $687. Check the full list of summer accommodations in Ossining.
There are 44 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with Casai.com.

Yes, here are some popular summer holiday rentals in Ossining that have a private or indoor pool:

Check all holiday rentals with a pool in Ossining on Casai.com.

Yes, We have 44 summer rental homes in Ossining and types of place to stay in Ossining include:

  • Vacation Homes: 44 available for rent
  • Villas: 44 Rentals available for rent
  • Holiday Apartments: 44 Rentals available for rent
  • Hotels with Suites: 44 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Ossining. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Ossining.