5 Best Hotels in Martha's Vineyard, Massachusetts

The inside of the former home of whaling captain Thomas Worth still evokes its late-18th-century origins—but with the boutique Lark Hotels group now in charge, the updated decor is best described as farmhouse chic, with airy spaces and vintage notes. Local art adorns the walls and shared spaces, like the lounge, are welcoming. White and grey bedspreads, natural woods, and wicker furniture keep rooms—some of which have harbor views—sleek and comfortable. Curated small plates for breakfast and afternoon snacks are a nice perk.

One of the best hotels in the Northeast, this stylish 1908 Arts & Crafts-style manor house marries "coastal grandma" chic with a personal touch. Innkeepers Annabelle and Simon Hunton are genial hosts that make guests feel like they're family friends on holiday. 

This 1870s Victorian has charm to spare, and feels like staying at a relative's home—albeit a discerning one, who appreciates Frette linens and Aveda bath products. Located on bustling Circuit Avenue, but at the quiet end of the street so you can still get some sleep, this ten-room inn has hosted such luminaries as Spike Lee, Woody Harrelson, and the late bell hooks. 

This rambling, sun-filled inn by the Aquinnah Cliffs stands alone on acres of moorland, a 10-minute walk from the beach. The clean and contemporary inn, with white walls and polished light-wood floors, is wrapped in windows revealing views of sea and sky in three directions; there are great views of the Gay Head Lighthouse from the wide porch and patio.

This chic, seasonal hotel consists of a 19th-century whaling captain's home and an adjacent newer building, located in the heart of Edgartown. 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.