12 Best Hotels in Martha's Vineyard, Massachusetts

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.

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.

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.

This 19th-century Gothic Revival boutique hotel blends the amenities and service of a luxury property with the ambience and charm of a small B&B with art and antiques that help capture the island's rural, seaside charm. Rooms, many of which overlook the spectacular gardens, are gracious and quite large by island standards; those on the upper floors have dormer windows. The front porch, filled with flowers and rocking chairs, is a perfect spot for reading or relaxing.

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. Richly appointed guest rooms, found in the house, restored barn, and stable from the 1800s, each have decorative schemes and antiques based on grand East Coast resort towns, from Key West to Bar Harbor; those in the outbuildings are airy and a bit more contemporary, some with decks and porches.

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 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.

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.

Located at the edge of Oak Bluffs' crazy-colorful collection of cottages, this is the last of the town's grand old hotels (circa1879), 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. 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.

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.