America’s Best Little Beach Towns

Chatham, Massachusetts
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Courtesy of Chatham Bars Inn

These uncrowded and unpretentious beach towns, from Florida to Hawaii, promise fun that's (could it be?) actually affordable.

Chatham, MA

21 of 23

Sitting at the sharp elbow of Cape Cod’s bent arm, the 16-square-mile Chatham has kept a lot of its old-school beach town charm by being conveniently off the beaten path. While its downtown boutiques lean toward the chichi, the folks here still know how to earn their keep; this is one of the few commercial fishing towns left on the Cape.

Stay: As the first luxury hotel on Cape Cod—launched in 1914 by a Boston stockbroker—Chatham Bars Inn still lives up to its street cred, decked out with Frette linens and sweeping Atlantic views. Take guided walks on the beach or at the nearby wildlife refuge, or play some croquet on the lawn.

Eat: For the classic lobster roll, head to the Chatham Pier Fish Market—formerly known as Nickerson’s Fish and Lobster, originally named after the town’s founder.

Katrina Brown Hunt

Chatham, Massachusetts

America’s Best Little Beach Towns

Chatham, MA

Sitting at the sharp elbow of Cape Cod’s bent arm, the 16-square-mile Chatham has kept a lot of its old-school beach town charm by being conveniently off the beaten path. While its downtown boutiques lean toward the chichi, the folks here still know how to earn their keep; this is one of the few commercial fishing towns left on the Cape.

Stay: As the first luxury hotel on Cape Cod—launched in 1914 by a Boston stockbroker—Chatham Bars Inn still lives up to its street cred, decked out with Frette linens and sweeping Atlantic views. Take guided walks on the beach or at the nearby wildlife refuge, or play some croquet on the lawn.

Eat: For the classic lobster roll, head to the Chatham Pier Fish Market—formerly known as Nickerson’s Fish and Lobster, originally named after the town’s founder.

Katrina Brown Hunt

Courtesy of Chatham Bars Inn
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