The variety of lodging options on Martha's Vineyard ranges from historic whaling captains' mansions filled with antiques to sprawling modern oceanfront hotels to cozy cottages in the woods. When choosing your accommodations, keep in mind that each town has a different personality: Oak Bluffs tends to cater to a younger, active, nightlife-oriented crowd; Edgartown is more subdued and dignified. Chilmark has beautiful beaches and miles of conservation lands, but not much of a downtown shopping area. Vineyard Haven provides a nice balance of downtown bustle and rustic charm. Bear in mind that many of the island's bed-and-breakfasts, set in vintage homes filled with art and antiques, have age restrictions—call ahead if you're traveling with a family. And remember that in July and August, the height of the summer season, minimum stays of as many as four nights may be required. If you're planning to visit for a week or more, consider renting a house.
You should make reservations for summer stays as far in advance as possible; late winter is not too early. Rates in season are very high but can fall by as much as 50% in the off-season. The Martha's Vineyard Chamber of Commerce maintains a listing of availability in the peak tourist season, from mid-June to mid-September.
