Recently rennovated antique Whaling Captain's house

Historic Skyemoor, originally built in 1694, is one of the 50 oldest houses on the island. Built by the Macy family, who arrived on Nantucket with the first settlers, Skyemoor is steeped in island history and culture, played host to Herman Melville and others, as well as served as the home of wealthy Whaling Captains throughout Nantucket’s whaling golden age. Today, Skyemoor is the perfect family home, having been tastefully and carefully renovated to provide modern conveniences without losing its antique roots. The house sits high up on Main Street, at the head of town and central to all that Nantucket has to offer. Charming shops, fine dining restaurants, and beautiful beaches are all just steps away. Experience Nantucket the way the island is meant to be, with an appreciation for her beauty, a nod to the past, and from the comfort of a welcoming and grand family home.

Please note: A signed rental agreement is required to finalize your reservation. Even if your booking request is accepted through VRBO, it is not fully confirmed until the rental agreement has been reviewed and signed. Instructions to complete the agreement will be provided immediately after booking
The Town of Nantucket or simply “Town” as many call it, is the epicenter of life on the island. Situated on the north side of the island around Nantucket Harbor, Town offers both natural beauty and historical charm. In the early 1800s, Nantucket was the whaling capital of the world. While the wharves and many structures in the commercial district were lost in the Great Fire of 1846, some still stand today and are thoughtfully preserved and accessible to the general public. Whether it is through tours of Nineteenth Century whaling captains’ homes, events at churches or the Athenaeum Library, or a visit to a museum, Town is steeped in history. Have you ever heard of Maria Mitchell, renowned astronomer and professor? How about Herman Melville’s Moby Dick? Surely you’ve read Nathaniel Philbrick’s In the Heart of the Sea, or seen the Hollywood blockbuster of the same name. Interestingly, Benjamin Franklin and Macy’s Department Store both have roots to Nantucket as well.

Restaurants, Shopping & Galleries

Along with historical charm, downtown Nantucket today is chock full of restaurants, shops, and galleries. A true gastronome’s paradise, Town offers all types of cuisine and levels of sophistication from A to Z. Whether you’re looking for Classic French, New American, Global, or something casual for the kids, you’re covered. In between meals, check out one of the many boutiques or art galleries as you stroll up and down narrow, beautifully landscaped cobblestoned streets. In the evening, there are many options for entertainment – whether it’s live music in a relaxed environment, or singing and dancing the night away in a swanky, lively spot.

Boating & Fishing

There are many active pursuits in Town, as well. Being located on the harbor, there are kayak, sailboat, and stand-up paddle board rentals. Take a walk down to Straight Wharf and reserve a sport-fishing charter or spend a day on a boat catching bass, bluefish, bonito, and maybe even see a few dolphins, whales, or sharks! There is also a Critter Cruise available for the kids.

Beaches & Biking

The Brant Point and Cliff areas are next to Town and offer several options for sunbathing at one of the north shore beaches. Also most of the bike paths are accessible from Town, making the rest of the island just a bike ride away!

Pets - not allowed


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