Nantucket is only about fourteen miles long, but where you stay shapes everything from your beach to your commute into town. Here is how the island actually breaks down.
Nantucket Town
Historic, cobblestoned, and walkable to the restaurants, shops, and ferries. It is the busiest part of the island and the easiest if you do not want to rely on a car; the harbor beaches nearby are calm enough for small kids.
Madaket (the west end)
Surf, wide ocean beach, and the island's best sunsets. It is about six miles from town, so you will want a car or a bike, and in return you get quiet and the big Atlantic.
Siasconset (Sconset, the east end)
Rose-covered cottages on the bluff, a lighthouse, and a genteel, sleepy pace. It is the farthest corner from town and all the more charming for it.
Surfside and Cisco (south shore)
The big-surf, beach-day side of the island, with Cisco Brewers nearby. Popular with a younger crowd and anyone who wants real waves. See our Nantucket waterfront rentals.
After the rental, the rest.
A flight in, a rental car for dune drives, a boutique hotel for the last night before the airport. The pieces that complete a coastal week.
Find a flight to the coast.
Compare hundreds of carriers via Booking.com, with free-cancellation fares on most routes.
Search flights →The car you'll actually want.
You will drive more than you think. A wagon or small SUV beats a compact for beach gear and dune trails.
Compare cars →The night before, in style.
Skylark curates design-led hotels and villas along the same coastlines, useful for the airport-side first or last night.
Discover Skylark →Sponsored.
Ten shores we vouch for.
Each town here is hand-picked, each rental vetted for real waterfront access. No algorithmic feeds.
Sleep By The Beach is a curated editorial guide. We earn commission on bookings made through links above, at no added cost to you. We never accept payment for placement.