You won’t find four-poster beds, floral wallpaper, or a doily on the toilet at the just-made-over Harbor View Hotel & Resort (from $350) in Edgartown. Though still wrapped in a white picket fence, the largest hotel on the island has officially gone modern: Its 900-square-foot suites are dressed up with black walnut floors, red cedar outdoor showers, and private gardens. Book suite 61 in the Captain Rowley cottage—it has a spacious stone patio—and lie out with some trashy beach reading.
The family-packed Winnetu Oceanside Resort (from $230) near Edgartown is a 250-yard stroll from South Beach, one of the loveliest strips of sand on the island. The resort’s rooms are freshly renovated and unfussy and loaded with domestic accoutrements like toasters, coffee-makers, and microwaves.
Partners Scott Jones and Kell Hicklin bought Lambert’s Cove Inn & Restaurant (from $220) in West Tisbury in January 2005 and immediately did away with the mounted geese and powder-blue décor. Now there are pale gold walls, ivory damask bedding, and plush dressing gowns, along with a heated, saltwater swimming pool and complimentary chairs, umbrellas, and towels for private Lambert’s beach.