Surround yourself with Edwardian opulence at Edgartown’s Charlotte Inn (from $325), where rich interiors feature carefully arranged displays of antique medicine boxes, porcelain tea sets and nineteenth-century oil paintings. A few modern touches—Bulgari toiletries, Bose stereo systems, and a well-chosen spread of Assouline art books and up-to-date issues of Vogue—ensure that rooms don’t feel too antiquated, while the no-cell-phone policy enforced in the hotel’s public spaces adds to its timeless charm.
Head a mile through the woods to reach the secluded Lambert’s Cove Inn (from $195), which sits on a seven-and-a-half-acre plot on the island’s northern tip. Each of the fifteen rooms is named after a town on the eastern coastline, including the medieval-looking Chesapeake, with toile-accented walls, a harlequin-painted chest, and a four-poster bed; and the rustic Savannah, whose original pine floors and matching sleigh bed recall a southern country lodge.
Grab a seat on the sprawling veranda that wraps around the scenic Harbor View Hotel (from $125) surrounded by stately nineteenth-century whaling captains’ homes. Its 114 rooms have a modern, beachy feel, and whether you end up in the basic Governor Mayhew building, whose rooms all come with private porches (but don’t face the water), the roomier main building, or the deluxe Captains Cottages, many of which offer fireplaces and kitchenettes, you’re never more than a minute away from the waterfront.