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.
Best for couples & first-timers
Edgartown harbor inns
Edgartown
Walk to the lighthouse, walk to dinner, walk to the Chappaquiddick ferry.
Best for families
Oak Bluffs boardwalk hotels
Oak Bluffs
Close to Inkwell Beach, the Flying Horses Carousel, and the Steamship dock.
Best for late ferries
Vineyard Haven harbor rooms
Vineyard Haven
Year-round town with bakeries, bookshops, and a short walk from the ferry.
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.
Best for a special occasion
Edgartown sea captains’ houses
Edgartown
Restored 18th-century houses turned into small luxury inns.