A wooden boardwalk winding through a forest with autumn foliage.

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Ossining cottages

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

1. Nyc-area Escape Near River, Trails & Mta!

Nyc-area Escape Near River, Trails & Mta!
3.0 star property
Ossining
$748 nightly
The price is $833
Oct 21 - Oct 22
Total with taxes and fees
Nyc-area Escape Near River, Trails & Mta!
A wooden deck with a railing overlooking a body of water and trees.

2. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
$372 nightly
The price is $425
Oct 3 - Oct 4
Total with taxes and fees
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A house with a view of a bridge and mountains.

3. 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, (146 reviews)
"We had a great stay!!"
United States
Jasmine
$280 nightly
The price is $331
Oct 6 - Oct 7
Total with taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
An outdoor patio with a stone wall, a wooden fence, and a table with chairs.

4. Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
$512 nightly
The price is $630
Oct 4 - Oct 5
Total with taxes and fees
Updated Home w/ Patio Half Mile to West Point
A wooden house with a stone pathway leading to a wooden deck.

5. 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, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
$1,519 nightly
The price is $1,719
Oct 18 - Oct 19
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A blue house with a porch, an American flag, and a brick pathway leading to the entrance.

6. 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
$591 nightly
The price is $698
Oct 22 - Oct 23
Total with taxes and fees
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

Amsterdam Hotel

Amsterdam Hotel

10/10 Excellent
"Room was clean and staff were very helpful"
Louisa 1-night trip
Posted 4 hours ago
Amsterdam Hotel

Find out more about Ossining

Ossining Cottages information

Number of reviews
171
Accommodation
53 Cottages
Lowest Price
$331
Highest Price
$1,719

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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