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Search Holiday Rentals in Ossining

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Ossining holiday rentals

House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Holiday Home in Ossining

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
The price is Rp6.882.415
Rp15.535.960 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

Aparthotel in Norwalk

The Mansion Hotel-style
2.5 star property
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is Rp1.500.840
Rp1.725.966 total
includes taxes & fees
11 Dec - 12 Dec
The Mansion Hotel-style
Apartment (1 Bedroom) | Interior
Gold Coast Getaway! Upscale Apt Near New Canaan

Apartment in West Norwalk

Gold Coast Getaway! Upscale Apt Near New Canaan
3.0 star property
The price is Rp3.668.720
Rp5.919.813 total
includes taxes & fees
14 Dec - 15 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan
Apartment (1 Bedroom) | Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Apartment in Greenwich

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
The price is Rp1.584.220
Rp4.109.133 total
includes taxes & fees
22 Dec - 23 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

10/10 Excellent
"Good place "
Gustavo 2-night trip
Posted 2 days ago
Ardsley Acres Hotel Westchester

Find out more about Ossining

Search for holiday rentals in Ossining on Expedia.co.id! 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 holiday rental in Ossining?

Yes, there are holiday rentals close to the most popular sights in Ossining, or you can select a more secluded 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.

What are some of the best holiday rentals that Ossining has to offer?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Ossining is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Ossining?

With 6 Expedia holiday rentals, you're guaranteed 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 holiday rental in Ossining like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Ossining. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.