A wooden boardwalk winding through a forest with autumn foliage.

Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Ossining vacation rentals

5 bedrooms

Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P63,259
P100,092 total
includes taxes & fees
Jul 13 - Jul 14
Summer Pool Oasis Custom Bar Arcade Pool Table
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ossining Hotel Reviews

Tarrytown House Estate

Tarrytown House Estate

10/10 Excellent
"Friendly, clean and comfortable. Rooms were sizeable for a standard hotel room, but the real draw is the property itself. Grounds are extremely pretty and tucked away from the hustle and bustle, and felt very safe. A cool place to just hang around if you have ample time. Seems to be popular for gathering and group retreats, if that is of interest, and seems an ideal place for that. I think for the money, it's a great deal, and would take it over a chain location any day. I highly recommend. Also, if you are taking the train into the city, Irvington station is actually closer than the Tarrytown station, and is, I want to say about a 10 minute drive away. I highly recommend this hotel, especially if ambiance is a factor for you. Enjoy!"
Aubrey 3-night trip
Posted 2 hours ago
Tarrytown House Estate

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia! You can easily find your home rentals, villas, holiday apartments in Ossining using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals in Ossining close to Labyrinth, or you can select a more remote option if you'd like a relaxing place to stay. Ossining is known for its restaurants and parks. Make sure you have time to check out the golf courses and university setting during your trip.

How many vacation rentals will I find in Ossining?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Ossining stay.

What’s there to see and do in Ossining?

Cultural attractions include Sing Sing Prison Museum and Ossining Historical Society, whereas Depot Square and Teatown Lake Reservation are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Hudson Hills Golf Course are other places to visit while you're in town.

What’s a vacation rental in Ossining like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Ossining. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for families.