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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Browse Select Ossining Cottages

Our top choices for Ossining cottages

Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
House (4 Bedrooms) | Interior

Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor

3.0 star property
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
Bright Cornwall-on-hudson Vacation Rental!
House (3 Bedrooms) | Interior

Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
Charming Highland Falls Home < 2 Mi to West Point!
House (4 Bedrooms) | Interior

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property
Charming Highland Falls Home < 2 Mi to West Point!
Dreamy Hudson Valley Cottage w/ State Park Views
Interior

Dreamy Hudson Valley Cottage w/ State Park Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Lakefront Brewster Vacation Rental w/ Private Dock
Cottage (3 Bedrooms) | Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Historic 1800s Cornwall-on-hudson Cottage!
Cottage (2 Bedrooms) | Interior

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Updated Home w/ Patio Half Mile to West Point
House (3 Bedrooms) | Interior

Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point
Outdoor Entertainment Areas: Spacious Katonah Gem!
House (3 Bedrooms) | Interior

Outdoor Entertainment Areas: Spacious Katonah Gem!

3.0 star property
Outdoor Entertainment Areas: Spacious Katonah Gem!
Home: 2 Mi to Thayer Gate at U.s. Military Academy
House (4 Bedrooms) | Interior

Home: 2 Mi to Thayer Gate at U.s. Military Academy

3.0 star property
Home: 2 Mi to Thayer Gate at U.s. Military Academy
3 Mi to Downtown: Spacious White Plains Home
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3.0 star property
3 Mi to Downtown: Spacious White Plains Home
Lake Carmel Access: Waterfront Home w/ Deck!
House (4 Bedrooms) | Interior

Lake Carmel Access: Waterfront Home w/ Deck!

3.0 star property
Lake Carmel Access: Waterfront Home w/ Deck!
Private Pool & Patio: Luxe Westchester Home!
House (Multiple Bedrooms) | Interior

Private Pool & Patio: Luxe Westchester Home!

3.0 star property
Private Pool & Patio: Luxe Westchester Home!
Charming Danbury Cottage w/ Lake Kenosia Access!
House (2 Bedrooms) | Interior

Charming Danbury Cottage w/ Lake Kenosia Access!

3.0 star property
Charming Danbury Cottage w/ Lake Kenosia Access!
Ossining Vacation Rental Near River, Trails & Mta!
House (5 Bedrooms) | Interior

Ossining Vacation Rental Near River, Trails & Mta!

3.0 star property
Ossining Vacation Rental Near River, Trails & Mta!
'the Glabin: Garrison Gem w/ Deck & Fire Pit!
House (3 Bedrooms) | Interior

'the Glabin: Garrison Gem w/ Deck & Fire Pit!

3.0 star property
'the Glabin: Garrison Gem w/ Deck & Fire Pit!
Charming Greenwich Escape Near Wooded Trails!
House (3 Bedrooms) | Interior

Charming Greenwich Escape Near Wooded Trails!

3.0 star property
Charming Greenwich Escape Near Wooded Trails!
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Interior

Lakefront New York Abode w/ Deck, Grill & Fire Pit

3.0 star property
Lakefront New York Abode w/ Deck, Grill & Fire Pit
Charming Bergenfield Retreat: 16 Mi to Manhattan!
Dining

Charming Bergenfield Retreat: 16 Mi to Manhattan!

3.0 star property
Charming Bergenfield Retreat: 16 Mi to Manhattan!
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Interior

Updated Getaway w/ Pool & Hot Tub on < 3 Acres!

3.0 star property
Updated Getaway w/ Pool & Hot Tub on < 3 Acres!
Vibrant Teaneck Home ~ 12 Mi to Manhattan!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Vibrant Teaneck Home ~ 12 Mi to Manhattan!

3.0 star property
Vibrant Teaneck Home ~ 12 Mi to Manhattan!
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

Find out more about Ossining

Find out more about Ossining

Ossining Cottages information

Number of reviews
Accommodation
28 Cottages
Lowest Price
Highest Price

Frequently asked questions

Why book your cottage in Ossining with Expedia?
We think that holidays 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 favourite 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 Centre, 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.