The next best thing to staying aboard your own sailboat is booking one of these weathered-shingle cottages along Nantucket Harbor's wharfs. Most of the 24 cottages (studio, one- and two-bedroom options) are spread along Old South Wharf and Swain's Wharf along Nantucket's quaint downtown. Once you've settled in, the sounds of seagulls, slapping halyards, and foghorns will make you feel like you're bobbing alone on a privately moored yacht.
Of course, there are lots of comforts here that would be hard to match at sea, like spacious sitting rooms decorated in maritime blue, white, and red, many with flat-screen TVs cleverly hidden inside pine armoires; the adjacent kitchenettes with their fridges and dining tables; or the slate-floored bathrooms with their walk-in showers and piles of fluffy towels. Just about every cottage has a private deck, where you can take the morning sun and watch boaties hoisting their sails for the day. If you are looking for a pet-friendly vacation spot on the island, their Woof Cottages are your best bet.