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Cottages in Ossining

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (111)
"Great place and host!"
$271 nightly
The price is $307
Jun 30 - Jul 1
Total includes taxes and fees
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Outdoor dining

Romantic retreat with stunning views of Croton River Gorge, a birder haven

10.0 out of 10, Exceptional, (3)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Second floor cottage apartment located in a private community.
Smart TV

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"This was a great property - location was perfect and the hosts were so easy to communicate with. It was exactly as pictured and was a great stay!"
Second floor cottage apartment located in a private community.
South Salem Vacation Rental w/ Furnished Deck!
Fridge, microwave, stovetop, dishwasher

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"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."
Charming 2 Bedroom Cottage in Peaceful New Canaan
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.
Fridge, microwave, oven, stovetop

This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

9.8 out of 10, Exceptional, (18)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (11)
"We really enjoyed this place and location. Everything as advertised. Clean, safe area with great parking, convenient to 95 and all of Stamford, comfortable bed, W/D steps away. "
Trendy 1 bedroom +loft apartment w/ parking
Historic 1800s Cornwall-On-Hudson Cottage!
Outdoor dining

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (26)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800s Cornwall-On-Hudson Cottage!
Lakefront Brewster Vacation Rental w/ Private Dock
TV, fireplace, books

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (5)
"Felt relaxed from first step in the door! Wonderful view, comfortable beds, helpful management, great kitchen! Loved the heated tile floor in main bath! Lots of birds to enjoy with books and binoculars for identifying. "
Lakefront Brewster Vacation Rental w/ Private Dock
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Smart TV, fireplace

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

9.6 out of 10, Exceptional, (13)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Historic 1800s Cornwall-on-hudson Cottage!
Interior

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Bright Cornwall-on-hudson Vacation Rental!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
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
Charming Highland Falls Home < 2 Mi to West Point!
Interior

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property
Charming Highland Falls Home < 2 Mi to West Point!
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Smart TV, computer monitors, printers

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"A cozy, well-maintained cottage, conveniently located near our son and his family who we were visiting. Modern appliances in the kitchen. Exterior and interior were as shown on VRBO. The property manager and owner were very helpful whenever we needed anything. Highly recommended. We would definitely like to stay here again whenever we visit our son."
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
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
Dreamy Hudson Valley Cottage w/ State Park Views
TV, fireplace, books

Dreamy Hudson Valley Cottage w/ State Park Views

9.6 out of 10, Exceptional, (14)
"Absolutely gorgeous house! Great location and a beautiful view from the porch. Would highly recommend to anyone. "
Dreamy Hudson Valley Cottage w/ State Park Views
Lakefront Brewster Vacation Rental w/ Private Dock
Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Carriage House: Romantic Hideaway near West Point
Fridge, microwave, oven, stovetop

Carriage House: Romantic Hideaway near West Point

10.0 out of 10, Exceptional, (1)
"This wonderful cottage has every amenity a traveler could want.. A beautiful modern kitchen, electric fireplace, lots of LED lighting, ample seating, extremely comfortable bed/pillows, and a huge smart tv. The neighborhood is gorgeous, and the property is located near many places worth visiting. Bear Mountain State Park, and the Storm King Art Center, just to name a few. We loved every minute we spent there. Catherine was a wonderful host who was always available to answer questions. We would...
Carriage House: Romantic Hideaway near West Point
Ridgefield Cottage: Walk to Town & Movie Theater!
Fridge, microwave, oven, stovetop

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!
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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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.