61+ Vacation Rentals in Ossining |
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Ossining Vacation Rentals, Hotels, & Places to Stay

About Ossining Vacation Rentals

There are more than 61 places to stay that are available in Ossining. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in Ossining.

Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. 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 Varoom's places in Ossining, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in Ossining. Places to stay near Ossining are 1131.06 ft² on average, with prices averaging US $610 a night.

Varoom helps you discover places to stay and suggests things to do to create great travel memories in Ossining. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Rental Accommodation Types in Ossining

Type Count
Vacation Homes 36
Holiday Apartments 10
Cottages 5
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ossining

★ Pro Tip: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in Ossining today.

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

Top Attractions Around Ossining, NY

Varoom offers a large selection of top attractions around Ossining . Research things to do on your vacation before you visit Ossining.


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

Other Places to Stay in Ossining, NY


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
Teatown Lake Reservation 46 Properties

Frequently Asked Questions About Ossining?

What are the top vacation rentals in Ossining?

We have scoured the web to find you options in Ossining. If you plan on staying near or in the Ossining area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the the Top Places to Stay in Ossining:

Which vacation homes in Ossining are best for families?

If you are looking for a place to stay that is family-friendly in Ossining, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in Ossining:

How many Varoom vacation rentals are available in Ossining?

Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom in 2025 is over 61 in the Ossining area, and still growing every day. When we combine listings from multiple websites and travel providers, Varoom can provide you with a diverse amount of choice of the best places to stay in Ossining. 


People Also Ask

There are 61 Ossining, NY Vacation Rentals

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