A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Ossining cottages

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
$640 nightly
The price is $713
Jul 27 - Jul 28
Total with taxes and fees
3 Mi to Downtown: Spacious White Plains Home
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, (140 reviews)
"We had a great stay!!"
United States
Jasmine
$282 nightly
The price is $333
Jul 23 - Jul 24
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
$498 nightly
The price is $549
Jul 27 - Jul 28
Total with taxes and fees
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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.
$676 nightly
The price is $766
Aug 18 - Aug 19
Total with taxes and fees
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)
"This house is the perfect private getaway! Everything was just as described and the host was super helpful. Will definitely stay again. "
United States
Anna F.
$1,194 nightly
The price is $1,351
Aug 13 - Aug 14
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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

Westchester Marriott

Westchester Marriott

10/10 Excellent
"We will definitely be staying here again on our next visit to NY!!"
Carly 2-night trip
Posted less than an hour ago
Westchester Marriott

Find out more about Ossining

Ossining Cottages information

Number of reviews
Accommodation
53 Cottages
Lowest Price
$713
Highest Price
$713

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.

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