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There are few things more “American” than summer in the Hamptons. But you don’t have to be a life-long Long Islander to associate the phrase with morning mimosas, soft shell crab, bike rides, salty air and a tan that lingers into fall. During summer months, the Hamptons is the place to be.

But don’t underestimate the magic of winter in the Hamptons. Winter is prime time for a weekend trip to the beach. Spend your evening snuggled up by an oceanside bonfire, take long walks on the beach and score deals that are simply unheard of during the warmer months — and you’ll get to do it without having to fight the crowds that flock en masse May through September.

Travel and Leisure writer Ann Shields highlights the fact that winter in the Hamptons is typically a much better experience for both tourists and locals. Instead of fighting crowds in shops, you can interact with local store owners. There’s no need to make dinner reservations weeks in advance or stake out a few square feet of space on the shore early in the morning.

On a winter trip to the Hamptons, the worst risk you run taking is inclement weather — although there are few better places to find yourself stuck indoors than in a cozy bed-and-breakfast by the shore. Here are our recommendations to make your weekend the best it can be.


Don’t poke around online trying to find a hotel room. Call your ideal hotel or bed and breakfast directly to inquire whether they have any off-season specials that are unpublished. According to Travel and Leisure, “nothing spurs innkeepers to generosity like empty rooms.” You could even score a last-minute upgrade to a suite at check-in.

You could also book a stay at a condo or beach house complete with a full kitchen, living spaces and other accommodations. Many beach houses are available for rent in winter, and owners often drop the rates to entice guests to stay.


The Hamptons are renowned for that feeling that time has somehow frozen in time decades ago. During the winter, that “frozen in time” feeling is even more prevalent, as it can feel a bit like a ghost town.

Don’t forget: it is the off-season, after all. Call shops and restaurants to make sure they’re open. Even the most popular restaurants can suffer financially due to the lack of visitors during winter; some have even been known to close a few hours early if they’ve got an empty house in February or March.


While the Hamptons’ infamous winter storms are beautiful to watch from indoors, be fully prepared to find yourself caught in a freezing gust of wind on a beach walk. Pack rain gear, warm clothing and enough books or magazines to entertain yourself indoors for a few hours. If you’re traveling with children, board games and other forms of entertainment are a must.


Whether you’re traveling from downtown Manhattan, Nassau County or JFK, a Long Island car service provides safe and luxurious transportation to your accommodations in the Hamptons. Not having to spend your Friday afternoon behind the wheel means more time for you to relax and reconnect. Let your chauffeur take care of the transportation so you can focus on getting into vacation mode.

Whether you’re a seasoned Hamptons tourist or paying your first visit to the town, a winter trip is affordable for nearly any budget. Hotel rooms in local bed and breakfasts that retail for upward of $250 a night in the summer months are less than $100 prior to April. Sure, you may have to swap your pedal pushers and swimsuit for a thick sweater and rain boots, but the ability to experience one of the most beautiful, pristine natural areas of the country is well worth it.