Search Vacation Homes in Ossining

"Very well appointed home a short walk from the West Point gate that met all of our needs for a weekend of catching up, going for walks and attending a wedding. Property is close to Storm King Art Center which is a great way to spend a beautiful afternoon. We lost power for 17 hours (neighborhood transformer blew) and the owners could not have been more helpful. Would highly recommend this house. "

"Review of VRBO Home - Our Rockbound Highland Rating: ⭐⭐⭐⭐⭐ (5/5) - Exceeded Expectations I recently stayed at a VRBO home that completely surpassed my expectations! The home was not only beautiful but incredibly comfortable, offering all the amenities promised in the listing. It felt like a home away from home and matched the online photos perfectly, which made our stay even more enjoyable. The check-in process was seamless, and the communication with the property manager was top-notch. This...

"We stayed here with our 3 dogs between Christmas and New Years. It is in a gorgeous neighborhood of sprawling estate homes. This property had tons of room to spread out. The yard is HIGE and completely fenced in. The rooms are decorated with the photography work of the owner and other interesting pieces. Plenty to do on site and not too far from the city. Lisa was great and even let our dogs out to potty so we could relax traveling into the city for a show and dinner. We would love to...

"Host was very accommodating and easy to communicate with!"

"Akuvi is an outstanding host. Prior to and during our stay he was immediately responsive to all of the messages/requests I sent him. The listing on VRBO is accurate and if you look at the description and pictures you'll get exactly what you're looking at"

"Host is kind and welcoming. The place is in a very quiet neighborhood. Plenty of street parking. 25 min from nyc. Highly recommend "

"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "

"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."

"Beautiful modern home with great views over the pond and woods. Super comfortable and many amenities. I really appreciated how well stocked the kitchen was with pots and pans that you can actually cook with compared to most VRBO's. Only drawback is that the area isn't really walkable. Busy road with minimal shoulder and you can't get down to the pond. We drove to a number of great hikes in the area though. Bonus: the woods behind the house were home to a couple great horned owls calling to...

"We had a wonderful stay at the Contemporary Cozy Cottage! Very modern amenities and appliances, and the kitchen had everything we needed!! Nadia always responded promptly, and answered all of my questions. The Cottage is located close to just about everything in the Peekskill, Cortlandt Manor, and Yorktown Heights area. And I would definitely recommend a short drive to the charming little town of Cold Spring which is not too far away. Thank you Nadia!"