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Holiday & Seasonal

Winter Getaway Deals and Staycation Ideas on Long Island

November 4, 2021

When people think about a visit to Long Island, they typically think of warm weather, beaches, and sunshine. But now is actually the perfect time to visit (or plan a staycation) that is sure to beat the winter doldrums

Hotels are offering special hotel packages that combine a stay with several fun options. You could book a romantic and relaxing package that includes spa services, or bring the whole family for a weekend of professional portrait photography.

The wineries are open year-round and a romantic trip to wine country is a great way to explore that region before the crowds of summer come pouring in. Several hotels offer overnight stays that include a wine tour and tastings. And for the especially hardy, you can book a golf weekend getaway and practice your shots before the summer starts.

Want to plan your own getaway that combines a hotel stay with a local attraction. Find things to do here. Or you can just keep it simple and make a plan to get together with family and/or friends for a ‘Pool Party Weekend.’ You find a hotel with an indoor pool and restaurant where you can shut out the cold and snow and relax in comfort. Order in, watch a movie, take a swim, enjoy the hot tub.

Want to get away with some friends? Book an East End wine tour that includes a shuttle to and from three handpicked vineyards, wine tastings, and a boxed lunch for the group.

The Inn and Spa at East Wind offers an East End Wine Adventure getaway that includes transportation and tasting at three Long Island Vineyards luxurious overnight accommodations in a Deluxe Double Queen Room; picnic lunch to go; dinner in Desmond’s Restaurant and a bottle of wine; breakfast in Myra’s Café; and a la carte services in the Spa & Salon – $50 value per person.

The Garden City Hotel’s Home for the Holidays package is the perfect excuse for a romantic getaway for two. It includes two breakfast vouchers and two drink vouchers for use in the King Bar, as well as the holiday-inspired housemade “Moose Tracks” treat any sweet tooth is guaranteed to love.

Couples can also head to The Inn at Fox Hollow and take advantage of the Suite Surrender package which includes an overnight stay in a luxury suite, champagne, roses and chocolates; dinner for two at Volpe restaurant at the Fox Hollow; and breakfast for two at the Inn at Fox Hollow. Or opt for the ultimate foodie tour package with the Inn at Fox Hollow’s Anthony Scotto Restaurant Dinner Package that includes an overnight stay, a $150 gift card toward Anthony Scotto Restaurants, a full American breakfast at the Inn, shuttle service, and concierge service for dinner reservations.

There are a lot of events still going on at our local museums. There’s a Norman Rockwell era exhibit at the Heckscher Museum, a Long Island in the 60s exhibit at the LI Museum, and a photography exhibit at the Nassau Museum of Art. Or plan an evening out at one of our local theaters and music halls where you’ll find everything from great musical performance comedy and live performances.

And some people might not realize it, but our wineries, breweries, and distilleries are open year-round for tastings and tours. Many feature live music during the winter months. You can arrange for transportation or a tour. Or, why not make a weekend of it and spend a winter getaway at a charming B&B.

There are a lot of other things to see and do on Long Island, even in the heart of winter. For more fun trip ideas and family-friendly activities, click here. 


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