Photo by Linda Zanetti

Search Holiday Rentals in Ossining

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Holiday Rentals in Ossining

Stamford Suites
Welcome to our reception area, featuring a polished reception desk, pendant light fixture, and patterned wallpaper with a geometric design.

Stamford Suites

4.0 star property
5.6 out of 10, (48)
"It was great relaxing stay"
The price is 3.632.983 ₫
4.177.930 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Stamford Suites
3BR Prime Luxury near NYC w Arcade Room
Terrace/patio

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
The price is 15.700.988 ₫
20.160.467 ₫ total
includes taxes & fees
9 Aug - 10 Aug
3BR Prime Luxury near NYC w Arcade Room
Global Luxury Suites White Plains
Enter a spacious lobby with a clear view of the outside, featuring a seating area with sofas and a coffee table, a flat-screen TV, and a reception desk.

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (31)
"This place a marvelous!! Very nice and clean!! The scenery of nature that I experienced when waking up was very refreshing!!"
Global Luxury Suites White Plains
Luxury Living in the Heart of NY
Enjoy meals at the glass dining table with a view of the city.

Luxury Living in the Heart of NY

4.0 star property
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
Luxury Living in the Heart of NY
Modern Luxury Home w GameRoom & Parking
Relax in this stylish living space with a sofa, armchair, and flat-screen TV.

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.0 out of 10, Good, (4)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
The price is 15.400.532 ₫
19.826.709 ₫ total
includes taxes & fees
10 Aug - 11 Aug
Modern Luxury Home w GameRoom & Parking
Cozy private room
Cozy retreat with a comfortable bed, desk, and chair, perfect for relaxation and work.

Cozy private room

2.0 star property
6.2 out of 10, (14)
"Please give me my money back. I no longer use the private room you rented. I went there and I couldn't get in. The code you gave me didn't work. I waited until 4 o'clock and I couldn't get in "
Cozy private room
Luxury Apartments by Hyatus at The Asher
Relax in a stylish living room with a plush sofa, dark fireplace, and large window offering a view of the outdoors.

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher
Luxury NY Home 3BR with Easy Parking
Relax in this stylish living room with a sofa, coffee table, and flat-screen TV.

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.0 out of 10, (4)
"I was fooled by the pictures. Upon check-in, they require to zelle cleaing fee. When I finally got inside, I found absolutely nothing lux about this property, no comfort and hospitality. The broken floor welcome me, all 4 beds are broken, only 2 TVs, moldy restroom, zero confort. They left 4 towels for 6 people for 6 nights. I had to request more towels. I had to scoop water fromthe shower to flush in the toilet because water would not drain. Half roll toilet paper was left. If you take...
Luxury NY Home 3BR with Easy Parking
Luxury NY Home with Free Parking
Enjoy cooking in this well-equipped kitchen with a stainless steel range, dishwasher, and double sink.

Luxury NY Home with Free Parking

4.0 star property
Luxury NY Home with Free Parking
Brand New Private Room
Relax in our stylish lobby, featuring a seating area, ambient lighting, and a timekeeping service.

Brand New Private Room

3.0 star property
4.0 out of 10, (1)
Brand New Private Room
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossining Hotel Reviews

La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

10/10 Excellent
"Great value with breakfast, staff is very nice and friendly but the room is noisy."
Han 1-night trip
Posted 20 hours ago
La Quinta Inn & Suites by Wyndham Stamford / New York City

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.

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 Depot Square and Ossining Dog Park 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.