Photo by Linda Zanetti

Ossining houses

We found 112 houses — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday home rentals in Ossining?
Book one of our 112 holiday home rentals and start organising your trip to Ossining. Whether you're staying in Crotonville, Pleasantville, Town of Mount Pleasant or another well-known neighbourhood, you'll discover the ideal house on Bookabach.
How much does it cost to stay in a holiday rental house in Ossining?
Your picture-perfect holiday home rental in Ossining is waiting to be discovered, with a range of prices from wallet-friendly accommodation to more upscale options. Enter your travel details to compare, making sure you find the best place for you and your guests.
When is the best time to rent a holiday house in Ossining?
That can all depend on the weather conditions you enjoy most, along with other considerations. Many visitors to Westchester County stay in an Ossining holiday home rental in July, when average temperatures range from 19ºC to 29ºC.
Where can I rent an Ossining holiday house with great views?
Slipping into holiday mode is a cinch when you book one of our Ossining houses with views of historic areas. From guests that seek adventure to those that want to simply sit back and relax, Bookabach has holiday home rentals with vistas that'll impress all types of travellers.
Does Ossining have any weekend house rentals?
Browse our weekend rentals and look forward to an exciting couple of days away. Our tips for booking the perfect house in Ossining? Be flexible when searching and change your dates until you find the holiday home rental that suits your needs.
Are there any pet-friendly house rentals in Ossining?
Use our handy filter tool to search for pet-friendly holiday home rentals in Ossining. To find a house rental that comes with amenities like an enclosed outdoor space or pet bedding, just check the box marked "Pets allowed."
What are the top things to do in Ossining?
From Bear Mountain State Park to Westchester County Centre and Van Cortlandt Manor, there's a bunch of exciting things to see and do during your family break to Ossining. With the sightseeing taken care of, we're here to help you book a holiday home rental that suits your style and budget.
Why should I book my holiday rental house with Bookabach?
When you choose a Bookabach holiday home rental, the only people you'll share your living space with are the people you bring along. It's only you, your family and the whole property to yourselves. Our flexible cancellation policies also mean you can book your rental house with peace of mind should your plans change.