Photo by Linda Zanetti

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
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Ossining

Summer Castle: Pool, Game Room, BBQ - Pet Friendly

8.6 out of 10, Excellent, (4)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
Summer Castle: Pool, Game Room, BBQ - Pet Friendly

Stamford Suites

4.0 star property
5.6 out of 10, (49)
"Excellent sleep"
The price is €130
includes taxes & fees
3 Sept - 4 Sept
Stamford Suites

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
The price is €660
includes taxes & fees
4 Sept - 5 Sept
3BR Prime Luxury near NYC w Arcade Room

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

9.0 out of 10, Wonderful, (7)
"Perfect place to rest. Excellent service! "
The price is €282
includes taxes & fees
4 Sept - 5 Sept
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Stunning 2BR next to Bronx Zoo

2.0 out of 10, (2)
"This property was at most the horrible experience. Property is not at all where it states on the website. When we arrived the ceiling was falling due to an old leakage and when I communicated with someone in charge of property, they said maintenance will come. We stood for a week and they came at the second to last day of our stay. It was cold every morning and the windows were patched with garbage bags. Everything was prone to disconnect from walls such as everything in bathroom. In addition to...
The price is €351
includes taxes & fees
24 Aug - 25 Aug
Stunning 2BR next to Bronx Zoo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (119)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is €273
includes taxes & fees
8 Sept - 9 Sept
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (36)
"Short trip. great place to stay . Very cozy . Family loved it "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

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 €617
includes taxes & fees
24 Aug - 25 Aug
Modern Luxury Home w GameRoom & Parking

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

8.0 out of 10, Very good, (16)
"Great place great location"
The price is €120
includes taxes & fees
27 Aug - 28 Aug
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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

Cozy Apartment-Just minutes from New York City

9.4 out of 10, Exceptional, (6)
"Nice place to stay "
Cozy Apartment-Just minutes from New York City

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (17)
"cleanliness. quiet. "
Luxury Apartments by Hyatus at The Asher

Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

10.0 out of 10, Exceptional, (1)
"I chose this apartment for its location primarily and it was a hit. Since we were traveling and staying for two weeks with a toddler and a new baby I was looking for it to also have an outdoor space, and it was wonderful as seen in the pictures. For personal reasons I had to change my dates a few days before my booking was coming up, the hosts had no problem to accommodate my needs. During our stay, we even had the opportunity to meet the neighbor next door and visit her garden. The neighborhood...
The price is €284
includes taxes & fees
8 Sept - 9 Sept
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

10.0 out of 10, Exceptional, (87)
"It was very nice "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

9.8 out of 10, Exceptional, (7)
"This was a great experience. Eche was an incredible communicator and seized quickly on any request we had and got it sorted almost before the phone call ended. The apartment is clean and lovely with a seriously undersold view of the reservoir, which sparkled in the morning sunlight through the wall-to-wall windows. WE WILL BE RETURNING TO THIS PROPERTY. And We still can’t believe we were in the middle of the Bronx. Thanks, Eche!"
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Romantic retreat with stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"I hesitate to sound too over the top in my praise of the Carriage House in Croton, but it’s difficult not to. The space is so comfortable, cozy, and filled with beautiful Mexican art pieces every where you look. Nothing has been forgotten by the hosts, who are charming and gracious, while allowing guests absolute privacy.The Carriage House is surrounded by natural beauty everywhere you look. From the Croton River below, to the wild turkeys in the morning and evening, and the omnipresent sound...
Romantic retreat with stunning views of Croton River Gorge, a birder haven
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

Top Ossining Hotel Reviews

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 Depot Square and Teatown Lake Reservation 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.