Montauk, New York
Courtesy Gurneys Montauk
Montauk may lure summer travelers with its sandy shores, surf spots, and resorts, but winter brings something even rarer—serenity. The roads, overrun with cars in summer, are clear and easy to navigate, making for a quick drive to year-round sites such as Montauk Point Lighthouse Museum or Deep Hollow Ranch. Plus, a handful of restaurants and resorts stay open for business despite the cold. Gurney’s Montauk turns up the heat with seasonal spa treatments, a Finnish-style rock sauna, a Russian steam room, and an array of wellness programming—all with a beautiful, snowy backdrop! Check out some charming small towns that are even cozier when it snows.
Courtesy The Nantucket Hotel
Once the world’s top whaling port, modern-day Nantucket retains much of its classic charm: Sweeping beaches, sand dunes, historic harbors, and seaside cottages. After the crowds have emptied out, this 50-square-mile island feels totally and utterly peaceful. Plus, off-peak prices at some of the island’s hottest properties mean you can experience New England luxury for a fraction of the cost. Winter rates at the famed Jared Coffin House—a stately brick mansion, once home to a prominent whaling merchant—start at $175. And you can stay at The Nantucket Hotel for around $230 (compared to $625 in the summer). Plus, there’s a cocktail hour in the outdoor hot tub and fondue by the fire pits.