64+ Luxury Vacation Rentals & Cabins in Ossining |
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Ossining Cabin Rentals

About Ossining Vacation Rentals

There are more than 64 incredible getaway rentals that are available in Ossining. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Ossining.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Ossining, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Ossining. Places to stay near Ossining are 1087.89 ft² on average, with prices averaging US $601 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Ossining. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Ossining

Type Count
Vacation Homes 36
Holiday Apartments 13
Cottages 5
B&B 1
Cabin Rentals 1
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ossining

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Ossining with Cabinns.com.

Weather in Ossining, NY

View the weather forecast for Ossining before booking your Ossining Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Ossining Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Ossining. Discover Top Attractions For Your Next Outdoor Adventure.


Sing Sing Correctional Facility
Thomas J. Watson Research Center
Sing Sing Prison Museum
Teatown Lake Reservation
Hudson Hills Golf Course
Ossining Historical Society
Nelson Park
Louis Engel Waterfront Park
Merchants Square
Pleasant Square
Snowden Avenue Park
Depot Square
Kitchawan Preserve
Woodbury Common Premium Outlets
Bear Mountain State Park
United States Military Academy
Capitol Theatre
Campgaw Mountain Ski Area
Empire City Casino
Palisades Center

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Nelson Park 94 Properties
Sing Sing Correctional Facility 91 Properties
Louis Engel Waterfront Park 88 Properties
Depot Square 85 Properties
Pleasant Square 77 Properties
Sing Sing Prison Museum 77 Properties
Snowden Avenue Park 77 Properties
Merchants Square 76 Properties
Ossining Historical Society 56 Properties
Maryknoll 51 Properties
Hudson Hills Golf Course 47 Properties
Crotonville 41 Properties

Frequently Asked Questions About Ossining?

What are the top cabins, lake houses & summer homes in Ossining?

We provide an array of great vacation destinations in Ossining. If you are looking to stay in or around the Ossining area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Ossining:

Which cabin rental, resort, or holiday home in Ossining is best for families?

Searching for a family-friendly cabin in Ossining? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Ossining?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 64 in the Ossining area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Ossining.


People Also Ask

There are 4 hotels in Ossining and 51 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Ossining