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Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Ossining vacation rentals

5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Vacation Home in Ossining

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
The price is P20,913
P50,992 total
includes taxes & fees
Jan 5 - Jan 6
Foliage at Westchester Manor - Near Sleepy Hollow
Lobby
Stamford Suites

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is P7,074
P8,135 total
includes taxes & fees
Jan 21 - Jan 22
Stamford Suites
Private kitchen
The Mansion Hotel-style

Aparthotel in West Norwalk

The Mansion Hotel-style
2.5 star property
8.2 out of 10, Very Good, (22)
"Great service and very clean 👌 "
United States
JEAN
The Mansion Hotel-style
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

DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

10/10 Excellent
"Clean room, staff was very nice."
Jonathan 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Nanuet

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:

  • View our selection of featured holiday rentals in Ossining
  • Use the map to find apartments and other holiday homes in the Ossining neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Ossining while they last

Look no further and take a look at our great range of rental properties in Ossining!

Frequently asked questions

Can I find a vacation rental in Ossining?

Yes, there are vacation rentals close to well known attractions in Ossining, or you can go with a more remote option if you're looking for a relaxing 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 6 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 Teatown Lake Reservation and Merchants Square are a couple of picturesque spots to enjoy the outdoors. Sing Sing Correctional Facility and Thomas J. Watson Research Center 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.