Boardwalk over marshland on the trail at Teatown Lake Reservation in Ossining, New York.

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Ossining cottages

Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is ￥31,987
￥53,816 total
includes taxes & fees
Jul 20 - Jul 21
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is ￥29,604
￥115,074 total
includes taxes & fees
Jul 14 - Jul 15
3 Mi to Downtown: Spacious White Plains Home
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is ￥50,743
￥116,432 total
includes taxes & fees
Jul 2 - Jul 3
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Property grounds

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (7 reviews)
"We did not use the fireplace or pool, but the home was amazing!"
United States
Jennifer D.
The price is ￥159,424
￥297,953 total
includes taxes & fees
Jul 6 - Jul 7
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
House (3 Bedrooms) | Interior

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
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

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

10/10 Excellent
"Great morning breakfast with our stay and they actually rotate the food items from day to day! Very quiet hotel and walking distance from Untermeyer Gardens and a few restaurants. The staff was super nice and very helpful. Great place!!!"
John 3-night trip
Posted 8 hours ago
Hampton Inn & Suites Yonkers

Find out more about Ossining

Ossining Cottages information

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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.