Black Point Inn

Just 15 minutes south of Portland on Prout’s Neck—the coastal tramping grounds of renowned Maine artist Winslow Homer—this 1878 inn with perfectly weathered cedar-shake shingles is one of the few Maine turn-of-the-century summer resorts still in operation. Some loyalists lament recent changes—including the loss of the elegant adjacent cottages once owned by rail barons (sold off as private homes in 2007). But an old-fashioned grandeur still infuses the lodge’s 25 rooms and suites, and etiquette is still taken seriously here; jackets are required for men in the formal dining room at dinner (which often includes regional standbys like New England clam chowder or butter-poached lobster). The inn’s outdoor assets are even more captivating—and include an enormous veranda with inviting wicker rockers, scenic 18-hole golf course, and the nearby Cliff Walk, a rocky one-mile trail where Homer liked to take in the seascapes he was so famous for painting.

Room to Book: The capacious corner Spinnaker Suite is the best in the house, with wraparound windows onto the bay and nautical details—maps, wood paneling—that recall a shipboard captain’s quarters.