This refined island inn is actually a complex of ivy-draped 18th- and 19th-century houses secreted among lovingly tended gardens. Over the past three decades, owners Gerret and Paula Conover have finessed the interiors to English country perfection, making high art of the William Morris-meets-gentleman's-hunt-club aesthetic. The inn's relaxed, come-as-you-are attitude belies what could easily be perceived as museum-style stuffiness; the studied refuge is not without quirky touches. Estate antiques—marble-top dressers, silver sets, standing clocks—fill the 25 elegant rooms; each has goose-down comforters, Wi-Fi, and its own luxurious (and often palatial) bath. The French-inspired restaurant, the Catch at the Terrace, pays homage to the sea, and the Edgartown Art Gallery—also owned by the Conovers—is just adjacent; be sure to take a moment to wander the painting-filled common rooms of the former merchant whaler's home. All of this, combined with gracious service and a no-young children-allowed policy, makes the Charlotte Inn a great choice for those in search of a civilized and romantic island retreat.
Insider Tip: The on-site restaurant is open only Friday-Sunday in winter; the French Bistro or The Grill on Main—both a short walk from the inn—are excellent alternatives.
Coziest Room to Book: The private carriage-house suite with dark green lacquered walls has a working fireplace in the living room, king-size bed, French doors, and bath with mahogany vanity and antique brass fixtures, as well as its own private entrance.