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Check prices for these dates

Next weekend
Jun 27 - Jun 29
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Jul 4 - Jul 6
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Jul 18 - Jul 20
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Aug 15 - Aug 17

Browse Select Ossining Condo Rentals

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Outdoor dining

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Enjoy the best of both worlds
Interior

Enjoy the best of both worlds

Enjoy the best of both worlds
Chic Peaceful Apt, Quiet & Safe w/Garage Parking
Property grounds

Chic Peaceful Apt, Quiet & Safe w/Garage Parking

2.5 star property
Chic Peaceful Apt, Quiet & Safe w/Garage Parking
ENGLEWOOD_CLEANReno 1bed WiFi_NO SMOKERS/VAPES/OUTDOOR SHOES _LongTerm Welcome.
2 bedrooms, WiFi, bed sheets

ENGLEWOOD_CLEANReno 1bed WiFi_NO SMOKERS/VAPES/OUTDOOR SHOES _LongTerm Welcome.

10.0 out of 10, Exceptional, (1)
"The host was wonderful, helpful, informative just all around accommodating. The unit was very clean, quiet and conveniently located near buses to get to and from NYC. Perfect choice for me. I will be utilizing this host in the near future."
ENGLEWOOD_CLEANReno 1bed WiFi_NO SMOKERS/VAPES/OUTDOOR SHOES _LongTerm Welcome.
Quaint Yonkers Condo - 1 Block to Hudson River!
Fridge, microwave, stovetop, dishwasher

Quaint Yonkers Condo - 1 Block to Hudson River!

8.0 out of 10, Very good, (13)
"They say a first impression can be your last and our first impression made it very hard to feel at ease in this unit. It looked like a construction zone. Dust was everywhere. They did have a cleaning person come in the next day and also provided air purifiers on request but still... my mom and I got daily headaches and nightly coughing fits. We are convinced in addition to the dust everywhere, there may be mold. We ended up extending our trip for a month. The unit was available but we booked...
Quaint Yonkers Condo - 1 Block to Hudson River!
Large Furnished Basement Studio with Bathroom, WiFi, AC, and Parking in Stamford
Interior

Large Furnished Basement Studio with Bathroom, WiFi, AC, and Parking in Stamford

Large Furnished Basement Studio with Bathroom, WiFi, AC, and Parking in Stamford
Hudson River Peaceful Getaway
Outdoor dining

Hudson River Peaceful Getaway

Hudson River Peaceful Getaway
Lovely Cozy apt near downtown, restaurants and shopping
Terrace/patio

Lovely Cozy apt near downtown, restaurants and shopping

10.0 out of 10, Exceptional, (2)
"First, Darwin was very responsive and flexible, after a 12 hr drive he was gracious enough to accommodate an early AM check in. Secondly, the location was ideal, close to downtown and grocery store. Lastly, the apartment itself had everything we needed, it was neat and spacious enough for our family. I would definitely recommend."
Lovely Cozy apt near downtown, restaurants and shopping
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

Why book your condo in Ossining with Expedia?
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How can I find cheap condos in Ossining?
Expedia can help you search for cheap condos in Ossining. To book a terrific stay in a matter of clicks, simply use our handy filter tool to tailor your search results by star rating, amenities and budget.
What is there to do in Ossining near my condo?
Ossining has enough experiences to keep you entertained for weeks, beginning with Sing Sing Correctional Facility. Thomas J. Watson Research Center, Louis Engel Waterfront Park and Ossining Historical Society are other wonderful attractions. If you're hanging around a while, Sing Sing Prison Museum and Teatown Lake Reservation are great additions to your itinerary.