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Southold Vacation Rentals (1)

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Explore Long Island’s North Fork:  Southold Vacation Rentals


Founded in 1640 by Puritans, Southold is arguably the oldest settled spot on Long Island‘s North Fork.  (The key word here is arguably; other settlements claim the honor as well.)  Aside from the hamlet of Southold, the town lines of Southold also encompass the areas of Laurel, Mattituck, Cutchogue, New Suffolk, Peconic, Greenport, East Marion, and Orient.  Fisher’s Island, which is six miles offshore of the Gull Islands in Long Island Sound, is also part of the town of Southold.  But for vacation rental purposes, we’ll refer to the hamlet of Southold on this page.


Where:  Southold is between Peconic and Greenport.  It’s about 45 miles from Long Island MacArthur Airport and 95 miles east of Manhattan.  The hamlet borders Little Peconic Bay, Southold Bay, and Long Island Sound; Shelter Island is just across the way.


What to Do and See:  Vineyards and wineries are a given for any North Fork destination.  Whether you rent a house, cottage, or villa, they’re never very far away.  There are also several public and private golf courses accessible from vacation rentals on the North Fork.  For amateur historians and lovers of maritime lore, the Horton’s Point Lighthouse and Nautical Museum is a must-see.