5 Long Island Staycation Destinations To Visit This Winter

long island staycation
Pack up the family for these local getaways. (Getty Images)

Who says Long Island is only fun in the summer? You don’t need the beach or warm weather to plan a staycation, and these five destinations prove that. 

From kid-friendly activities like the aquarium to adult-only adventures like beer and wine tastings, Long Island has much to offer for a weekend of excitement. Plus, the hotels, bars, and restaurants will welcome visitors with open arms after a long day of exploring.

Whether you enjoy the thrill of a casino or the tranquility of an art museum, Long Island can deliver a staycation you won’t soon forget. With lots to do indoors this winter, you won’t know where to visit first. Here are five destinations to check out this season.


Stay at the Hyatt Place Long Island/East End, where you can relax at the indoor pool or work up a sweat in the fitness center. But the best reason to visit is for the Long Island Aquarium and Exhibition Center, located right next door. 

The hotel offers a “Land and Sea” package through Dec. 31 that includes aquarium tickets starting at $170 per night. The aquarium has a 120,000-gallon shark tank, sea lion shows, animals you can touch, and more than 100 other exhibits.

Fun for the whole family doesn’t end there because Riverhead is also home to the Railroad Museum of Long Island. Plus, you’ll want to pop over to nearby Flanders for a Long Island favorite, the Big Duck gift shop and visitor center.


If you’re feeling fancy, Southold is the place for you. You can easily bounce between each of the North Fork town’s wineries and warm up with a variety of tastings.

Start at Duck Walk Vineyards, then make your way up the wine trail. Next along the strip is Mattebella Vineyards. Then, make your reservation at Sparkling Pointe winery and sip some bubbly inside its enchanting tasting house. Other options include Mudd’s Vineyard, One Woman Wines & Vineyards, and the Old Field Vineyards in the area.

For meals, the North Fork Table & Inn is your spot. And for a place to stay, there’s the Southold Beach Motel or hotels in nearby Greenport.


Try your luck at Jake’s 58 Hotel and Casino. It’s the perfect winter escape because your place to eat, play, and sleep is all in one location. 

For the kids, there’s a Dave & Buster’s just a minute’s drive from Jake’s 58. There are also plenty of restaurants along Veterans Memorial Highway, and other hotel options such as the Hampton Inn and Residence Inn by Marriott.


Devour a slice of Long Island history when you visit Huntington’s Oheka Castle. Book a hotel stay at this historic mansion, which is the second-largest private residence built in the United States. 

If exploring this massive estate isn’t enough, Huntington also offers the Heckscher Art Museum, as well as quaint cafes, restaurants, and plenty of shopping along Main Street in the downtown.


What better way to get cozy this winter than with a freshly brewed beer in a rustic-style tasting tavern? Glen Cove’s Garvies Point Brewery and Noble Savage Brewing Company have craft beer lovers covered.

Glen Cove is also chock-full of history, with several museums to visit, including the Holocaust Memorial and Tolerance Center of Nassau County, Garvies Point Museum and Preserve, and North Shore Historical Museum.

Be sure to visit Glen Cove Salt Cave, a relaxing, holistic health spa offering immersive salt therapy. And rest your eyes at The Mansion at Glen Cove, another historic estate-turned-hotel with lofty amenities, such as a fitness center, spa, yoga studio, and indoor heated pool.

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