From harbor inns to farmhouse weeks

Where to Stay

From harbor inns to farmhouse weeks

The right town depends on how you travel. A first weekend almost always works better in Edgartown or Oak Bluffs. A second trip rewards a quieter week up-island with a kitchen and a porch.

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Best for couples & first-timers

Edgartown harbor inns

Edgartown

Walk to the lighthouse, walk to dinner, walk to the Chappaquiddick ferry.

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[theme_image src=”oak-bluffs.jpg” alt=”Oak Bluffs cottages”]

Best for families

Oak Bluffs boardwalk hotels

Oak Bluffs

Close to Inkwell Beach, the Flying Horses Carousel, and the Steamship dock.

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Best for late ferries

Vineyard Haven harbor rooms

Vineyard Haven

Year-round town with bakeries, bookshops, and a short walk from the ferry.

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[theme_image src=”biking.jpg” alt=”Tree-lined up-island road”]

Best for a quiet week

Up-island farmhouse rentals

Chilmark & West Tisbury

A kitchen, a porch, stone walls along the road, and a real sense of quiet.

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[theme_image src=”edgartown-light.jpg” alt=”Edgartown”]

Best for a special occasion

Edgartown sea captains’ houses

Edgartown

Restored 18th-century houses turned into small luxury inns.

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