Lambert's Cove Inn (very expensive)
Lambert's quaint rooms are in the main house, carriage house, and guesthouse of a cozy estate that dates back to 1790. The on-site restaurant offers some of the best dining on the island.
Surfside Motel (moderate)
Bargain accommodations aren't exactly easy to come by on the Vineyard, which is why we appreciate the Surfside. For less than many other places, you get a nice, clean room, and the waterfront locale is just steps from the ferry, Flying Horses Carousel, and other Oak Bluffs establishments.
Wine Spectator praised this elegant eatery, saying it has "one of the most outstanding restaurant wine lists in the world." The food isn't bad, either, thanks to chef/owner Christian Thornton's globally inspired menu of steamed dumplings with tomato-ginger chutney, braised pork belly with petite French lentils, and the like.
Menemsha Fish Market (inexpensive)
This seaside market, which has been shelling out everything from tuna to tilapia since 1946, also serves heaping hot bowls of some of the best lobster bisque you've ever tasted.
You can't talk about Martha's Vineyard without mentioning a vineyard. This one, open for tours and tastings, produces Chardonnay, Chenin Blanc, and other fine wines, as well as specialty foods like mustards, vinegars, and chutneys.
Granary Gallery at the Red Barn
The Granary showcases a variety of artists, from local stone-carver Ben Cabot to internationally renowned photographer Margaret Bourke-White. On Sunday afternoons, patrons gather in the sculpture garden out back for the popular weekly artist reception.Off-season? Isn't it cold in the off-season? The island in the fall is just magic. That's my favorite time of year there. The air is definitely crisp then, but what's great is that you can still get those last few warm weekends, when the beach is still so nice. The biggest summer crowds are gone [by then], and you kind of get the island back; a lot of the businesses - the coffee shops, the bookstores, and the restaurants - are still open. Once it gets to be winter, a lot of things close down.