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Ossining Holiday Rentals

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Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Ossining

Summer Castle: Pool, Game Room, BBQ - Pet Friendly
Outdoor banquet area

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

8.0 out of 10, Very good, (3)
"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. "
The price is HK$6,429
HK$10,821 total
includes taxes & fees
21 Jul - 22 Jul
Summer Castle: Pool, Game Room, BBQ - Pet Friendly
Stamford Suites
Lobby

Stamford Suites

4.0 star property
5.8 out of 10, (44)
"You walk 2 blocks and bunch of stores and great restaurants. Try Bari restaurant"
The price is HK$1,208
HK$1,389 total
includes taxes & fees
14 Jul - 15 Jul
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 HK$4,702
HK$6,038 total
includes taxes & fees
14 Jul - 15 Jul
3BR Prime Luxury near NYC w Arcade Room
Global Luxury Suites White Plains
Reception

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
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (116)
"The greatest spot anyone could imagine. We will be back in the fall for the beautiful colors. "
The price is HK$1,476
HK$2,389 total
includes taxes & fees
15 Jul - 16 Jul
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Cozy Apartment-Just minutes from New York City
Smart TV

Cozy Apartment-Just minutes from New York City

9.4 out of 10, Exceptional, (3)
"Nice place to stay "
Cozy Apartment-Just minutes from New York City
Waterfront Retreat Center for Health & Wellness
Property grounds

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (60)
"This is my second state at the New Dawn house and it was just as wonderful as last year. I can't think of a better place for a large gathering in the Bronx area. "
Waterfront Retreat Center for Health & Wellness
Brand New Private Room
32-inch flat-screen TV with cable channels, TV

Brand New Private Room

3.0 star property
4.0 out of 10, (1)
Brand New Private Room
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Terrace/patio

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 HK$742
HK$1,058 total
includes taxes & fees
16 Jul - 17 Jul
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Stylish Stay in City’s Best Spot- The Perfect Stay
Outdoor dining

Stylish Stay in City’s Best Spot- The Perfect Stay

2.0 out of 10, (1)
"I arrived in New York on 6-22-25 I requested the check in information in which the host refused to give. She stated the cleaner hadn't showed up to clean the property so she gave me another address. Well this place had multiple stairs and was located on the 2nd floor which couldn't accommodate the group I was with. When I informed the host she gave me another address which was smaller with one bathroom. Smaller than the original one booked. After explaining that this wouldn't work the host...
Stylish Stay in City’s Best Spot- The Perfect Stay
Stunning 2BR next to Bronx Zoo
Fridge, microwave, oven, stovetop

Stunning 2BR next to Bronx Zoo

2.0 out of 10, (1)
"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 HK$1,405
HK$3,302 total
includes taxes & fees
20 Jul - 21 Jul
Stunning 2BR next to Bronx Zoo
Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, Private, 1 hr NYC
Dining

Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, Private, 1 hr NYC

10.0 out of 10, Exceptional, (77)
"Lovely stay at large and clean home with great kitchen and pool area. Lots of room for everyone and attentive hosts"
Simply Unforgettable 8br, Pool, Pets, Hot Tub, Fire Pit, Private, 1 hr NYC
Luxury Apartments by Hyatus at The Asher
Lounge

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
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (82)
"The house was super clean and very easy to take care of while we were here. It was perfect for a remote getaway, hiking and just being quiet. "
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Living area

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

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office
Luxury NY Home 3BR with Easy Parking
Living area

Luxury NY Home 3BR with Easy Parking

3.0 star property
3.4 out of 10, (3)
"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...
The price is HK$3,368
HK$4,545 total
includes taxes & fees
14 Jul - 15 Jul
Luxury NY Home 3BR with Easy Parking
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Smart TV

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

10.0 out of 10, Exceptional, (5)
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Private lake escape
Outdoor pool

Private lake escape

Private lake escape
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.
Exterior

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.
Modern Luxury Home w GameRoom & Parking
Living area

Modern Luxury Home w GameRoom & Parking

3.0 star property
6.8 out of 10, (3)
"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 HK$4,082
HK$5,344 total
includes taxes & fees
15 Jul - 16 Jul
Modern Luxury Home w GameRoom & Parking
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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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 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.