Photo by Linda Zanetti

Search Ossining Cottage Rentals from CA $258

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Ossining Cottages

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Stroll through a serene residential setting surrounded by a lush lawn, a tree, and a picturesque bridge.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (118)
"Nice view on the top of the mountain….I admired the river with the bridge and the surroundings until late in the night. The accommodation was excellent, we had everything we needed.… we are thinking of coming back sometime…."
The price is CA $272
CA $441 total
includes taxes & fees
Aug 4 - Aug 5
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Second floor cottage apartment located in a private community.
Two-story house with a wooden staircase and porch, set amidst lush greenery and a paved driveway.

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.
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Enjoy al fresco dining in this outdoor space, complete with a grill and comfortable seating for two.

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
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Walk along the weathered boardwalk to a serene body of water surrounded by lush trees and vibrant flowers.

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

10.0 out of 10, Exceptional, (5)
Romantic retreat with stunning views of Croton River Gorge, a birder haven
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!
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
Charming 2 Bedroom Cottage in Peaceful New Canaan
Enjoy serene views from this deck overlooking a well-maintained lawn and trees.

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
Historic 1800s Cornwall-On-Hudson Cottage!
Stately home surrounded by a well-manicured lawn and lush trees, featuring a charming front porch and a small garden.

Historic 1800s Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (29)
"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
Set amidst lush greenery, this house offers a serene atmosphere with a large outdoor area and a bench.

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (7)
"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
Peaceful Cottage with Grill | Walk to Lake
Exterior

Peaceful Cottage with Grill | Walk to Lake

9.8 out of 10, Exceptional, (19)
"This property was great. Clean, roomy and about 1/2 hour from West Point."
The price is CA $258
CA $686 total
includes taxes & fees
Aug 4 - Aug 5
Peaceful Cottage with Grill | Walk to Lake
Trendy 1 bedroom +loft apartment w/ parking
Relax in this inviting living room with a comfortable sofa, flat-screen TV, and cozy rug.

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking
South Salem Vacation Rental w/ Furnished Deck!
Cozy cabin with a front porch and lush surroundings.

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 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!
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
Dreamy Hudson Valley Cottage w/ State Park Views
Relax on the covered porch with a comfortable seating area and enjoy the view of the surrounding trees.

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
Dreamy Hudson Valley Cottage w/ State Park Views
Relax on the porch with a view of the surrounding forest, featuring a seating area with a chair and ottoman.

Dreamy Hudson Valley Cottage w/ State Park Views

9.6 out of 10, Exceptional, (14)
"We had a quiet and relaxing stay. Great location for exploring Cold Spring and Beacon"
Dreamy Hudson Valley Cottage w/ State Park Views
Ridgefield Cottage: Walk to Town & Movie Theater!
Single-story house with a paved driveway and white picket fence.

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!
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 Pound Ridge Cottage, 2 Beds, Fully Furnished
Escape to a secluded cabin surrounded by a lush forest, featuring a gabled roof and arched window.

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossining Hotel Reviews

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Clean."
KYUNG 1-night trip
Posted 1 day ago
Royal Regency Hotel