Photo by Linda Zanetti

Ossining Holiday Rentals

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Holiday Rentals in Ossining

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is AU$299
includes taxes & fees
26 Nov - 27 Nov
Stamford Suites

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"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

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is AU$388
includes taxes & fees
30 Nov - 1 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (26)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

The Subterranean Haven

9.0 out of 10, Wonderful, (6)
"Great communication, house was perfect in size and location"
The price is AU$567
includes taxes & fees
2 Dec - 3 Dec
The Subterranean Haven

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (8)
"We were transported and had a wonderful family celebration at this magical location so close to the City. It is exactly as it appears in the photos, spacious comfortable with extraordinary views and a great pool. Very easy to check in and very attentive manager!"
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

9.8 out of 10, Exceptional, (46)
"Wonderful property in a very quiet neighborhood 20 minutes from Metlife Stadium. Lisa provided lots of very helpful information. We used the hot tub, steam room and sauna. The decor was very nice! We would definitely stay there again as it is very close to Metlife and also very close to NYC."
Country Carriage House ONLY 15 MIN TO NYC Great for Families, Couples, Reunions

Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY

9.2 out of 10, Wonderful, (11)
"The apartment was exactly as stated and shown in the photos"
Stylish 3-bedroom 3rd fl Apt in Mount Vernon, NY

Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor

6.0 out of 10, (4)
"Everything match the details, nice and cozy quite neighborhood to be so closed to the Bronx"
Lovely 2 Bedrooms Short term Rental Unit on a 2nd Floor

Mini Garden-Apartment near New York City

Mini Garden-Apartment near New York City

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (11)
"This property was even more beautiful than it appeared in the photos. The wooded backyard was also spacious and lovely. We were so happy with the view of the lake and how peaceful the space was. The owners are easy to communicate with and prompt to respond. We will absolutely be going back. "
The price is AU$1,293
includes taxes & fees
26 Nov - 27 Nov
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

Cozy private room

2.0 star property
7.0 out of 10, Good, (7)
"Property locked upon arrival. No communication of any kind re checking in, no email, no return of multiple phone calls at all. I needed to find another hotel and seek a full refund, which was given by Expedia. Terrible travel experience, beware."
Cozy private room

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

10.0 out of 10, Exceptional, (74)
"This place was a great place for us to stay on our vacation. Secluded outside of the city, and a short drive down a gravel road, it really feels that you're lost in the woods, but in a good way. If you're up to visit the Gunks, Angry Orchard, the Hudson river, love the beauty of the outdoors, and have other family or friends to visit in the area, definitely consider this home. Host was very responsive and had everything ready for us."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (18)
"Great space. Clean sheets and towels. Wonderful shower. Great balcony I highly recommend!"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

20%off LongTerm discount- Comfy Entire 2 Bedroom Apartment - 30 min train to NYC

7.2 out of 10, Good, (10)
"The place was clean, not perfectly clean but very much so (I'm fairly picky about that). The kitchen and fridge were well-equipped. If I were forced to criticize anything, it would be that the downstairs neighbors could be a bit quieter later in the evening (the worst was bouncing balls around indoors at 11PM) - but that's something the host will have limited control over and we and our kids managed to sleep well enough anyway. Communication with the host was speedy and overall everything was...
The price is AU$493
includes taxes & fees
26 Nov - 27 Nov
20%off LongTerm discount- Comfy Entire 2 Bedroom Apartment - 30 min train to NYC

Yonkers Apt w/ Balcony: Walk to Train Station!

8.6 out of 10, Excellent, (26)
"Great stay and accessible to public transportation however Renter beware of the STEEP hills that you will need to walk. We walked from both stations and we got killed by the steep roads to get to the property. The property was overall in a clean and maintained status. Maybe just need to have the shower curtains changed but it was overall a great choice. "
Yonkers Apt w/ Balcony: Walk to Train Station!

1-bedroom vacation home 12 minutes from Bronx Zoo

9.8 out of 10, Exceptional, (22)
"We stayed for several days because the price was 1/4 the price of staying in the city. The apartment was clean and private. Parking was free and we ran in the neighborhood each morning. Everyone we met was very nice. "
1-bedroom vacation home 12 minutes from Bronx Zoo

Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

6.6 out of 10, (7)
"Really well kept basement unit."
The price is AU$286
includes taxes & fees
26 Nov - 27 Nov
Spacious & Cozy 1st Floor & Basement Apartment 15 min from NYC!

Cheerful Home in Yonkers NY

7.6 out of 10, Good, (4)
"To summarize without too many details we had to be placed in a hotel. I am sure once this house is given proper detailed updating it will be worth it. Please be clear you will Uber a lot unless you have a car or someone to pick you up from Yonkers."
The price is AU$817
includes taxes & fees
30 Nov - 1 Dec
Cheerful Home in Yonkers NY
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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Other types of properties in Ossining you may be interested in

Armoni Inn & Suites

3.5 star property
6.0 out of 10, (1692)
"Nice and clean "
The price is AU$110
includes taxes & fees
10 Dec - 11 Dec
Armoni Inn & Suites

Royal Regency Hotel

3.5 star property
8.2 out of 10, Very good, (1832)
"Relaxing and clean Hotel "
The price is AU$224
includes taxes & fees
15 Dec - 16 Dec
Royal Regency Hotel

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1525)
"Very clean and well kept. "
The price is AU$178
includes taxes & fees
26 Nov - 27 Nov
Amsterdam Hotel
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.
Beautiful view of the beach with palm trees

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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?

Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Ossining is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Ossining?

With 7 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 Louis Engel Waterfront Park 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.