A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Ossining cottages

A two-story house with a front yard, a staircase, and a covered outdoor seating area.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is ₩366,844
₩1,095,116 total
includes taxes & fees
Oct 21 - Oct 22
Snow Days & City Escapes: Spacious Ossining Home
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

2. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
The price is ₩498,531
₩938,408 total
includes taxes & fees
Oct 22 - Oct 23
Bright Cornwall-on-hudson Vacation Rental!
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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Top Ossining Hotel Reviews

Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

10/10 Excellent
"Tout était parfait merci à tous"
Marc 1-night trip
Posted 6 hours ago
Sleepy Hollow Hotel, a Dolce by Wyndham

Find out more about Ossining

Ossining Cottages information

Number of reviews
1
Accommodation
35 Cottages
Lowest Price
₩938,408
Highest Price
₩1,095,116

Frequently asked questions

Why book your cottage in Ossining with Expedia?
We think that vacations should be a walk in the park, so if you're chasing cottages in Ossining at an affordable price, Expedia can help. Stick to the budget and go for a wallet-friendly option surrounded by wilderness, or splurge on an upmarket cottage to spoil your favorite people.
How can I find cheap cottages in Ossining?
Expedia is here to help you look for cheap cottages in Ossining. To book the perfect stay in just a few clicks, try out the filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Ossining near my cottage?
Ossining has enough experiences to keep you going for weeks, beginning with Sing Sing Correctional Facility. Thomas J. Watson Research Center, Louis Engel Waterfront Park and Ossining Historical Society are other awesome attractions. If you're lingering longer, Sing Sing Prison Museum and Teatown Lake Reservation will cap off your itinerary nicely.