51+ Vacation Rentals & Holiday Homes in Ossining |
  1. USA
  2. New York
  3. White Plains
  4. Ossining

Ossining Accommodations - Hotels & Rentals

About Ossining Vacation Rentals

Discover More than 51 Incredible Getaway Rentals Available in Ossining. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Ossining.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Ossining, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Ossining. The Average Size of Places to Stay Near Ossining is 481.78 ft², with Prices Averaging US $564 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Ossining. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

Show more
Show less

Top Hotels & Vacation Rentals in Ossining

Type Count
Vacation Homes 14
Holiday Apartments 11
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Ossining

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Ossining with Online Reservations.

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 OssiningGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World OssiningGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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 & Vacation Rentals in these Cities and Neighborhoods


Maryknoll 69 Properties
Hudson Hills Golf Course 66 Properties
Kitchawan Preserve 64 Properties
Thomas J. Watson Research Center 62 Properties
Crotonville 33 Properties
Ossining Historical Society 27 Properties
Louis Engel Waterfront Park 27 Properties
Merchants Square 25 Properties
Pleasant Square 25 Properties
Sing Sing Prison Museum 25 Properties
Snowden Avenue Park 25 Properties
Depot Square 25 Properties

Frequently Asked Questions About Ossining?

What are the top hotels, lake houses & vacation rentals 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 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:

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

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 51 in the Ossining area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Ossining.


People Also Ask

Online Reservation in Ossining

Recently Booked Hotels, Resorts, or Rentals in Ossining