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Ossining Hotels, Resorts, and Rentals

About Ossining Vacation Rentals

There are more than 66 places to stay in Ossining that are available. These options include hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many places to stay in Ossining.

Are you seeking a last-minute hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With Hotala Ossining, you can quickly compare different options to find the hottest deals with a single click. Looking for a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Ossining. Places to stay near Ossining are 1054.92 ft² on average, with prices averaging CA $844 a night.

Hotala makes it easy to find and compare hotels, resorts, and holiday rentals in Ossining with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your reservation today.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in Ossining

Type Count
Vacation Homes 37
Holiday Apartments 13
Cottages 6
B&B 1
Cabin Rentals 1
Others 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Ossining

★ Pro Tip: Hotala.ca has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in Ossining.

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

Stay Near Ossining's Top Attractions

Hotala.ca can help you find hotels, resorts, and rentals near many of Ossining's top attractions, neighborhoods, and points of interest.


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 Hotels, Resorts, and Rentals Nearby 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 hotels or resorts in Ossining?

You have a lot of choices in or near Ossining. If you need a hotel in the Ossining area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in Ossining:

How many vacation rentals have private pools in Ossining?

There are 1 accommodation options with private pools in or near Ossining. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:

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

At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2025 is over 66 in the Ossining area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in Ossining.


People Also Ask

There are 4 hotels in Ossining and 52 rentals

Recently Booked Hotels, Resorts, or Rentals in Ossining