Each of the six towns on the Vineyard has a distinct character and distinct characters, and so do the island's individual B & Bs and country inns. The handful below distinguish themselves not only for how much they reflect the flavor of their town, but also because each adjoins a restaurant that makes it unnecessary to wander too far come evening.
To help select the ambience that suits you, here is a quick review of island geography and vocabulary: “down-island” means the eastern end, the towns of Vineyard Haven, Oak Bluffs and Edgartown, bustling places with vibrant main streets. West Tisbury is “mid-island,” surrounded by pastoral splendor; its village center is a church, a town hall, a library, the Field Gallery and Alley's General Store. To the west — “up-island” — are Chilmark and Aquinnah, rural settlements of sheep-dotted meadows and woodlands.
Since some B&Bs are situated in dry towns, bring your own spirits to dinner at all the establishments below except for The Charlotte Inn.
Those who missed the Vineyard summer may look the wiser by planning now for the island fall. Rates and crowds drop noticeably while the water temperatures do not, thanks to warming Gulf Stream currents.
The Charlotte Inn
The title of a book about the inn best sums up its ambience: “Behind the Times on Purpose.” On a side street in Edgartown — lined with whaling captains' huge white mansions that never let you forget its moneyed past or its moneyed present — this Edwardian building ushers you into a bygone era. Antique fixtures, furnishings and 19th-century art of the fox hunt genre cram the three parlors and rooms of the main house, as well as the four other buildings.
 Gery and Paula Conover, who have owned and lived at the inn since 1970, don't take reservations by e-mail. They prohibit cellphone use in public areas and do not accommodate groups or children younger than 14. The inn, a Relais & Châteaux property, still doesn't have its own Web site (though you can view rooms at the site listed below). Reservations are hard to get for its 25 rooms. “If it's not broke, don't fix it,” Mr. Conover said.
Little nooks, ponds and bench areas tucked into unlikely corners make the grounds feel larger than they are. Mr. Conover tends the gardens using antique tools.
The chef, Chris Parsons, whose Catch restaurant in Winchester, Mass., has garnered praise in the Boston area, took over the Charlotte Inn's restaurant in May, renaming it Catch at the Terrace. The dining room is one of the most romantic settings for a meal on the island. Tall windows and a glassed-in patio area with ferns and fountains give it a greenhouse feel; the walls are chockablock with quirky antiques like a row of old wooden mailboxes.
Mr. Parsons, a fourth-generation fly fisherman, not surprisingly focuses on fish. Herb-roasted Atlantic cod surrounded by Menemsha lobster and Wellfleet clams, all afloat in a sea of lemon-thyme broth, is excellent. He shows what he can do with local meats in a tender red-wine-braised lamb from Allen Farm in Chilmark, with chanterelle mushrooms and Macumber turnips.
Rooms are $295 to $695, suites $695 to $950; starting Nov. 2, rooms are $295 to $495, suites $550 to $595. 27 South Summer Street, Edgartown; (508) 627-4151; www.relaischateaux.com/charlotte.
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