9 Best Hotels in Martha's Vineyard, Massachusetts

A narrow road winds through pine woods and beside creeper-covered stone walls to this posh, handsomely designed farmhouse inn (1790) surrounded by extraordinary gardens and old stone walls set on 8 acres. Guest rooms are named after island farms, and feature fresh, airy, slightly modern farmhouse--style design. Some have decks and porches. 

One of the best hotels in the Northeast, this stylish 1908 Arts and 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. 

From the moment you walk up to the dark-wood Scottish barrister's desk to check in at this regal 1864 inn, you'll be surrounded by the trappings and customs of a bygone era—beautiful antique furnishings, objets d'art, and paintings fill the property. All guest rooms have hair dryers and robes; those in the carriage house have fireplaces and French doors that open into the brick courtyard, as well as private patios. One room even has a baby grand piano.

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 coastal 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.

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.

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.

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.