The Sullivan House is the beach home you wish you could inherit. A turn-of-the-century landmark, it's set on a hill with expansive views of the island and the sea. The house itself has six bedrooms and is surrounded by five other cottages and beach houses that can also be rented. In all, you can sleep about 50 guests in your own little seashore colony.
Guest Activities: There's something for everyone on the island—beaches, hiking trails, a Victorian-era town, and an active boating scene. Rent a posse of mopeds or bicycles to tour the island, or tour by sea, reserving a private fleet of kayaks or chartering a yacht.
Wedding 411: Weddings are a familiar event here, and the same company that owns the property also owns the island's biggest catering service and party rental business. (Clambakes featuring fresh lobster and the island's famous clam chowder are popular choices.) Set up a tent on the lawn, and weddings up to about 350 guests can be accommodated.
Fees: $1,425 per night, with a two-night minimum. Additional site fee for weddings: about $3,000 for a party for 150 guests; includes the china, glassware, and linen rental.