Pat & Chuck Blackley / Alamy
Brian Kevin
August 22, 2014

How’s this for history? Maine’s southern coast is home to what may well be the oldest hotel in America, Kennebunk’s Seaside Inn, welcoming guests since at least 1660. Okay, so a lodging establishment that predates the extinction of the dodo bird is a bit of an anomaly, but there are still centuries worth of stories waiting inside the quarried granite walls and beneath the wood-shingled roofs of Maine’s venerable inns. Some retain the stately character of their Gilded Age past, while others thrive at the intersection of past and present, with updated interiors and modern amenities that accent rather than disguise their historic charm. Maine’s nautical past alone is the stuff of a thousand legends, with so many dramatic cupolas and widow’s walks adorning the grand coastal mansions, it seems like every house with an ocean view once belonged to a doomed sea captain. These five hotels have a timeless appeal.

Portland Regency Hotel & Spa

Once one of New England’s most fortified armories, the imposing brick Regency indeed looks impregnable, and the large brick fireplaces in the suites are a (cozy) throwback to its military past. These days, the building is less about muskets and canons than massages and cocktails, although the latter are served in the Armory Lounge.

Old Granite Inn

This eight-room bed-and-breakfast takes its name from the locally quarried stone that make up its impressive gray façade. Built in 1840, the Federal Colonial building has been an inn for thirty years, and the rooms blend period furniture with a flair for contemporary design evident in the linens, art, and lighting.

Seaside Inn

This family friendly beachside hotel has been renovated…a zillion times. The earliest document referencing an inn on this site dates to 1660, and the current owners represent the ninth (!) generation of innkeepers. America’s oldest hotel is light and breezy with few frills—other than the outdoor hot tub looking out over the ocean.

Newagen Seaside Inn

Not to be confused with that other Seaside Inn (a common moniker in coastal Maine), Newagen has hosted guests like Frank Sinatra and Rachel Carson, who came to the tip of this cape seeking ocean views and ends-of-the-earth solitude. The hotel opened in 1816, but today’s white clapboards and colonial columns went up following a 1943 fire.

The Claremont Hotel

Predating Acadia National Park by 35 years, the 1884 Claremont is a throwback to the early days of Mount Desert Island leisure and opulence. There’s a vibe of old-school gentility to a croquet game on the immense lawn that slopes towards the water—as well as to watching it from a wicker-backed rocking chair on the wraparound porch. 

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