3 Best Hotels in Martha's Vineyard, Massachusetts

There has been a hostelry on this conveniently located Main Street site just above Vineyard Haven Harbor since 1794. The indoor pool and well-equipped health club (with sauna and steam room) are open to everyone for a fee. Apart from the cheerful, sunny rooms—some with balconies, gas fireplaces, and soaking tubs—the cupola deck provides a stunning spot for a respite, affording sweeping views of the harbor, the town, and the lagoon that stretches between Vineyard Haven and Oak Bluffs.

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.

This chic, seasonal hotel consists of a 19th-century whaling captain's home and an adjacent newer building, located in the heart of Edgartown. Guest rooms are set on two floors. The Sydney is part of the Edgartown Collection—including the Edgartown Inn, the Richard, and the Christopher—located within walking distance of each other, and sharing some of the same features, like a complimentary small-plates breakfast and a fun, coastal vibe.