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Luxury rentals in Nantucket

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Top-rated luxury holiday rentals in Nantucket

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Three Old Farm
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Hilltop Estate

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All about Nantucket

All About Nantucket

The Little Grey Lady Of The Sea

Once the center of America’s whaling industry, Nantucket island transformed into an elite east coast vacation getaway with an average house price of $2.3 million. Colonial buildings and quaint cottages line the main streets of Nantucket Town, while on the outskirts, some of the country’s most impressive mansions populate this nautical paradise. If you love fresh seafood, days on the beach, and evening walks along Main Street; you already love Nantucket.

How to get to the island

Nantucket Memorial Airport, with only 3 runways, shows off its efficiency in the summertime, logging more daily activity than Logan Airport in Boston. If you’re flying in, it’s quickest and easiest to connect through Boston or New York City. If you’d rather bring a vehicle or simply prefer to travel by sea, Hy-line Cruises and the Steamship Authority offer year-round service from Hyannis, MA. And, Freedom Cruise Line and Seastreak provide seasonal high-speed ferries from New Bedford, New York City, New Jersey, and Harwich Port.

Getting around Nantucket

A rich history in whaling

From the late 1700s to the mid 18s, Nantucket’s growing wealth was defined by its whaling industry. Wives of sea captains would spend nerve-wracking evenings staring off into the horizon, hoping to see their husband’s boats coming into port. The town is entrenched in nautical lore, most famously illustrated by Herman Melville in the American classic, Moby Dick. Today, the Nantucket Whaling Museum, a former spermaceti candle factory, shows off the island’s history in observation halls packed with artifacts, photos, and even a 46-foot sperm whale skeleton. The museum is right downtown, so it’s an easy stop before dinner in the Historic District.

Award-winning wine and unbelievably fresh seafood

From the cobblestone streets of the Historic District to the seaside neighborhood around Brant Point, Nantucket is packed with some of New England’s best restaurants. Needless to say, the seafood is the star of the show. The Lobster Bloody Mary at Brant Point Grill is a brunch staple. The raw bar at Cru is famous for its grilled swordfish, lobster rolls, and sweeping views of the megayachts docked in the harbor. If you’re in the mood to discover a new favorite wine with your seafood dinner, Topper’s is well-known for its perfect pairings, with 1,450 wines on hand, and 23 consecutive Wine Spectator Grand Awards under their belt. After dinner, you’ll surely see the locals flocking towards The Juice Bar for milkshakes, waffle cones, and signature smoothies. It’s a good idea to follow.

Golden hour at the Island’s most iconic lighthouse

Established in 1746, the Brant Point Light Station has had its fair share of growing pains. The first 3 light towers burned down, a few were condemned, and one simply blew over, a testament to the power of the Atlantic. But, in 1901, Nantucket got its most popular, postcard-worthy beacon. Today, the Brant Point Lighthouse, a national historic site, stands tall, proud, and bright at the end of Easton Street, about a 10-minute walk from the Whaling Museum.

Classic cars, independent film, and culinary creativity are on display… It’s festival season.

From late April until the end of June, Nantucket is set in festival mode. It all kicks off with the Daffodil Festival. Celebrate spring with an antique car parade, tailgate picnic, and the iconic Nantucket flower show. Next, join world-famous chefs and winemakers for the Food and Wine Festival in May. Then, get your tickets early for screenings at June’s Nantucket Film Festival, showcasing everything from up-and-coming independents to Hollywood blockbusters.

Daytripping from Nantucket to Martha’s Vineyard

Nantucket’s neighbor island, Martha’s Vineyard, is about an hour west on the Oak Bluffs Ferry. Once you step off the boat, it’s just a short walk to the eclectic shops, seafood restaurants, and ice cream bars on Oak Bluff’s busiest one-way, Circuit Avenue. Next, check out the gingerbread cottages in Oak Bluffs Campground, take the kids to Flying Horses Carousel, or stop for a swim at Inkwell Beach. If you’re up for a little adventure, rent some bikes and ride to the border of Edgartown and Oak Bluffs on Beach Road, where you’ll find “Jaws Bridge.” It’s customary for visitors to jump...into the water where they shot Jaws.

Nantucket Beach Guide

North Shore

South Shore

East and West

Nantucket vacation rentals, in and out of town

Staying close to the action, you’ll find most of our Nantucket luxury rentals in the Town and Brant Point neighborhoods. As you move towards the iconic lighthouse, the scenery becomes more about yachts, beaches, and ocean views, while the downtown area is all about short walks to the ice cream shop and quaint cottage lined streets off the main strip. Both neighborhoods are within walking or biking distance of each other, and most of Nantucket’s attractions. If you’d rather a more secluded getaway, keep an eye on the city skyline from the extremely desirable Monomoy area, just off Nantucket Harbour. Calm waters, uninterrupted ocean views, and the island’s best shell fishing make this area quite the catch.

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