Outside New York City, the volume is in the Catskills and Hudson Valley, the Adirondacks, the Finger Lakes, and the North Fork and Hamptons on Long Island. These are seasonal, often rural or coastal, and frequently older homes. New York City itself is effectively closed to investment short-term rentals.
Winter upstate, water on the coastUpstate, the perils are northern: freeze, ice dams, lake-effect snow load, and the long vacancy stretches of a seasonal cabin. On the East End, it flips to coastal wind and flood. Older rural housing and well-and-septic systems add their own exposure, and remote Adirondack properties face long fire-response times.
Upstate New York claims fail most often on freeze in a seasonally empty home and on remote fire response; on Long Island, on the coastal flood line. The common thread is a standard policy that assumes occupancy and excludes flood. Confirm vacancy and freeze terms upstate, flood coverage on the coast, and your fire-response distance everywhere.
New York splits sharply. New York City runs the strictest law in the country: Local Law 18 requires registration with the Office of Special Enforcement, limits rentals to a host’s primary residence with the host present, caps guests at two, and effectively prohibits investment short-term rentals, listings fell more than 90 percent after it took effect. The state added its own registry law in 2024. Upstate is the opposite, the Catskills, Finger Lakes, and North Fork generally welcome investment properties, though the Hamptons towns and individual villages are adding permits and caps. Outside the city, regulation is a town-by-town question; confirm it before you buy.