From our home, it's about a 3 hour drive to Woods Hole, MA, then a 45-minute ferry ride to the island of Martha's Vineyard. The island is about 20 miles long at it's widest point, and is home to around 15,000 year-round residents, swelling to over 100,000 during the summers.
We made it just ahead of the main busy season, and the weather was rainy during our time there, so we were able to explore without negotiating a massive rush of other tourists/vacationers.
There are hundreds of these "gingerbread" houses in the town of Oak Bluffs.
Oak Bluff town common, near the ferry port.
Among other things, the Vineyard is known for its historic lighthouses. This is located outside of Edgartown.