3 Best Hotels in Martha's Vineyard, Massachusetts

A departure from most properties on the island, the contemporary Winnetu—styled after the grand multistory resorts of the Gilded Age—has successfully struck a fine balance in that it both encourages families and provides a contemporary seaside-resort experience for couples. In addition to options in the main inn, which all have kitchens and decks or patios with views of gardens, the two pools (and hot tub), or of the Atlantic, there are 68 three- to five-bedroom homes available to rent by the week; it's a great option for large families, and all resort amenities are shared.

After more than 130 years of pampering guests, including Steven Spielberg and the Jaws cast and crew in 1975, this historic hotel is a true island classic. The gray-shingled 1891 Victorian building certainly looks the part, with its wraparound veranda, gazebo, and beautifully landscaped grounds. The resort includes two other historic buildings and an array of cottages. Whether you stay in the main house, the Roxana, or a cottage, expect Frette linens, plush robes, Molton Brown toiletries, use of beach towels, and perks like complimentary use of bicycles, shuttles to town or the beach, a saltwater pool, and hotel-led activities. The extensive children's summer program has a full roster of activities for kids; also offered are yoga and fitness classes, as well as lawn games for the whole family.

Located at the edge of Oak Bluffs' crazy-colorful collection of cottages, this is the last of the town's grand old hotels (circa 1879), reimagined with a playful summer camp theme. Rooms are spread among two buildings; the best feature is an expansive porch with rocking chairs that overlook the harbor. Families will appreciate Camp Canteen, open 24/7 for snacks.