Though it reached its economic and political preeminence during the age of whaling, Nantucket has a firm grip on the popular imagination even today, in an era where the public is keener on saving whales than hunting them. 200 years ago, the island inspired the writings of Herman Melville. Today, it is still popular with Boston’s elite for a weekend away. The specific nature of Nantucket’s appeal has changed over the centuries, but it has persisted.
The island is often compared to another off of Cape Cod: Martha’s Vineyard. Rightly so, as both are gorgeous sea-swept masses with rich histories (Nantucket’s is best preserved in its whaling museum, a must-see for any lover of Moby Dick). However, Nantucket is smaller, more remote, and sees about half as many visitors. It is a quieter place where visitors can walk and bike to everything, but no less rich or memorable.
Whether you’re primarily interested in seafood, seafaring, or idling on the beach, Nantucket has much to offer. Getting to the island requires careful planning whether you intend to travel by plane or ferry. But, getting around the small island is quite simple, whether by bike or shuttle.
Here are 10 cottage Vrbo vacation homes on Nantucket, splendid but quaint homes which match the character of the island itself. They cover the breadth of Nantucket and each is near a beach.
Eliza Cottage On The Harbor$875/nightly avg
Discover the indelible quaintness of Nantucket from the comfort of this well-placed cottage. The home is next door to the island’s famous White Elephant Hotel and a short walk from the high street. Its position on the harbor makes it an excellent way to take in the sail-filled skyline which dominates the island. What’s more, it has several special comforts put in place to elevate guest experiences. These include brand-new cookware, custom Matouk bedding, and a Sonos sound system. The cottage has one bedroom with a king bed connected to a bathroom with double vanity. Though best suited for couples, this one-bedroom vacation rental can accommodate four thanks to a pull-out sofa in the living room.
Remote Homestead On Private Island$343/nightly avg
Plenty of people visit Nantucket every year, but few get to experience the island as it was before modernity came. Experience a different way of life in splendid seclusion at this historic post-and-beam structure on Tuckernuck Island. Tuckernuck is a private island about half an hour from Nantucket Town, ideal for a romantic weekend getaway. The caretaker will give you a ride, but it’s up to you to take the 10-minute walk through empty wind-swept fields to reach the home (though portage for luggage can also be arranged). Do so and you’ll find an old but updated home in a style no longer seen. Great for a couple or small family, the home has a bedroom with two twins on the main level, plus a loft with two double beds.
West End Cottage 50 Yards From The Pier$678/nightly avg
This Madaket cottage is yet another great way to take in the sun, stars, and water views which have inspired those disembarking at Nantucket. Renovated in 2020, the home has excellent views of the island’s quieter western harbor but is just a few miles from the busier streets of Nantucket Town. It has a verdant yard, a sunswept deck, and comfortable modern interiors. There are two queen bedrooms and one room with a bunk bed.
Historic Oldtown Cottage$651/nightly avg
A much-admired example of Nantucket architecture, this quiet cottage sits within the bounds of the historic town. With a lush yard surrounded by high hedges, guests might briefly forget the cobbled streets surrounding the home. The 19th-century floor plan has been preserved, making a stay in the cottage akin to a trip into the past. The home has a queen bedroom on each floor and is also home to an impressive (and situationally appropriate) art collection.
Cabin And Cottage At The Point O’Breakers$545/nightly avg
A stay at this splendid property just yards away from Madequecham Beach promises waves of reinvigoration that will wash over the entire family. It consists of a two-story cottage and a detached private cabin with a queen bedroom and a tangible aura of coziness. The main building has two bedrooms with pairs of twin beds and a master. All are located on the second level and have excellent ocean views. Guests can walk a few hundred feet through untouched moorland and find themselves on one of the quiet sandy beaches that characterize Nantucket’s southern shores.
Pet-Friendly Home In Nantucket’s Historic Heart$600/nightly avg
Despite a regular flow of tourists, Nantucket Town still has many quiet streets that recall the island’s past as an economic, rather than a tourist hub. This lovely rental property is on one such street, a short walk from the town’s historic sites, museums, and family-friendly attractions. The two-story building’s front is adorned with flowers and the interior is furnished in a homey style. The patio, protected by hedges, makes for an excellent spot to grill or simply take in the weather. There is one bedroom on each floor.
Large Cottage On Monomoy Harbor$1,057/nightly avg
This four-bedroom cottage will appease the pickiest group of travelers. It has harbor views, a spacious backyard, and boasts private trails which take amblers to the storied waters of the Nantucket Sound. Surrounded by old trees and hedges of privet, the property promises privacy as well as comfort. Sunlight fills the wood-paneled living room and radiates across the four bedrooms (which include two queens, a room with two twins, and an upstairs double bedroom serviced by internal and external staircases, perfect for a family vacation). This great location even has an outdoor shower and a grill for those tranquil summer days on the island.
Restored 19th Century Home On The Wharf$1,700/nightly avg
Once occupied by generations of hardy New England fisherfolk, this waterfront home has been lovingly restored. It is an excellent way to explore Nantucket’s history while enjoying all the pleasures available to guests today. The town’s center is right outside your door and close to the sea, in case you want to do some fishing. The interiors are a satisfying mix of historic fixtures and modern appliances. The oceanfront large deck is just one of many great places to spend one’s time.
Rose Covered Cottage On Pocomo Harbor$1,567/nightly avg
Situated on a quiet corner of the island, vacation photographs from this Nantucket cottage resemble scenes from New England’s past. Guests can take a few steps to find themselves on a Head Harbor beach, or take a longer stroll to the open ocean at Quidnet beach, adjacent to the Coskata-Coatue Wildlife Refuge. Whether you make use of the home’s kayaks or not, your time on the water is sure to captivate the senses and activate wistful and romantic feelings. The location and views of natural beauty are really the highlight, but the cottage’s interior spaces are cozy as well and the handy amenities will ensure your stay is stress-free.
Beautiful Home At Smith Point$1,179/nightly avg
Enjoy down-to-earth living on the water’s edge at this gorgeous beach house on the western end of Nantucket Island. Surrounded by sand and the ever-present sounds of the sea, a stay at this home strikes at the core of the Nantucket experience. It has a lived-in feel and is the perfect place for a reflective retreat, just as it is for a rowdy one. The ground floor has two bedrooms with twin and bunk beds while the master takes up the top level. Situated as it is right on the beach, the outdoor spaces are, of course, splendid.
To discover even more things to do in and around Nantucket, check out: