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Ossining Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Ossining vacation rentals

House | 5 bedrooms
NEW 45 Wolden Rd Ossining NY 10562

Vacation Home in Ossining

NEW 45 Wolden Rd Ossining NY 10562
2.0 star property
The price is NT$9,847
NT$26,261 total
includes taxes & fees
Jan 12 - Jan 13
NEW 45 Wolden Rd Ossining NY 10562
Living area
Luxe 1BR Oasis - Prime NY Stay

Apartment in Bryn Mawr

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
The price is NT$3,463
NT$8,566 total
includes taxes & fees
Jan 19 - Jan 20
Luxe 1BR Oasis - Prime NY Stay
Living area
Single Family 3BR Home Game Room Parking

Villa in Bryn Mawr

Single Family 3BR Home Game Room Parking
4.0 star property
Single Family 3BR Home Game Room Parking
Private kitchen
Luxury 1BR located in Prime Yonkers Area

Apartment in Bryn Mawr

Luxury 1BR located in Prime Yonkers Area
2.0 star property
The price is NT$3,117
NT$8,179 total
includes taxes & fees
Jan 19 - Jan 20
Luxury 1BR located in Prime Yonkers Area
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

Hampton Inn White Plains/Tarrytown

Hampton Inn White Plains/Tarrytown

10/10 Excellent
"Front desk staff very nice. Thank you William. Room is clean and quiet. "
Andy 1-night trip
Posted 2 days ago
Hampton Inn White Plains/Tarrytown

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.