As the name implies, the hotel faces out to picturesque Edgartown Harbor, while the center of Edgartown (think ice cream shops, seafood restaurants and art galleries) is only a five-minute walk away.
In fact, the Harbor View offers three choices for accommodations: the hotel itself, the Governor Mayhew Building and a string of Cape Cod Captain's Cottages dotted around the property. But for the classic, New England-style grand hotel experience, we'd recommend booking a room at the hotel itself, which offers all the regular amenities (room service, WiFi, an outdoor pool) and even has its own fancy restaurant, Water Street on the ground-floor. There, guests can munch on locally-caught seafood and fish, and produce brought in from farms around the island.
Of course, if it's the beach you're after, then the hotel wins in that department too, since there's a strip of beach right in front of the building—not to mention a beautiful old 19th century lighthouse, which occasionally opens to allow people to peek inside.
The rooms themselves are fairly simple, but between the private balconies and waterfront views, you're not likely to be spending much time in bed anyway. To second that: along the front side of the building is a wraparound porch, which is ideal for pre- or post-dinner drinks, and where we'd happily spend an entire evening just gazing out at the sea.
Rates this September start at around $210/night and $245/night for a room in the Gov Mayhew Building and the main hotel, respectively; or $640/night for a private cottage suite.