Greater Portland + Casco Bay

Hotels in Greater Portland + Casco Bay

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.

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.

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.

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.

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.

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.

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.