Greater Portland + Casco Bay

Hotels in Greater Portland + Casco Bay

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.

Set on the edge of the cobbled Old Port neighborhood, this opened-in-2003 hotel offers upscale (if somewhat corporate) accommodations just steps from some of the city’s best bars, restaurants, and shopping.

Book a sunny room in this 1835 home within walking distance of the Old Port.

Bargain-hunters, outdoorsy types, and persnickety hotel-goers all like this comfortable inn within short walking distance of bustling Freeport, a.k.a. outlet central (170+ shops) and home to L. L. Bean, which has been outfitting fly-fisherman, campers, and preppies since 1912.

This seasonal property on Maine’s central coast is open from April through October and resides on a grassy knoll along Penobscot Bay’s rocky shore.

Just minutes from Portland's scenic Old Port in the Western Promenade neighborhood—renowned for its stately mid-19th-century homes designed by New England architect John Calvin Stevens—this stylish inn stands out from the city's more fusty accommodations.

Chebeague Island Inn is a tasteful, pared-down vision of grand seaside living—massive fieldstone fireplace, board games, and overstuffed chairs in the great room lobby and a wide porch made for watching boats and sipping stiff cocktails at sunset.

Connected by a private boardwalk to sandy, three-mile-long Crescent Beach, this five-acre resort reopened in June 2008 after a multimillion-dollar eco-renovation.