A few blocks north of downtown Edgartown, this friendly 19th-century Gothic Revival–style B&B has plenty of antiques and chintz like the nearby Charlotte Inn, but is airier and slightly less expensive (befitting its less central location). The 17 individually decorated rooms, freshened up during a recent renovation, have charming details: painted four-posters, dormered windows, skylights, small sitting areas, antique silver hairbrushes laid out on side tables, and a cow motif that reminds owner Maggie White of the ones she keeps on her West Tisbury farm. Adding to the homey tone are the chocolate-chip pecan-cinnamon cookies at afternoon tea, berry pancakes for breakfast, box lunches for the beach, and Maggie's Labradors, which will cheer you up if you've left your own pooch at home. But there's no lack of mod cons: AC, cable, Wi-Fi, a sauna and spa treatments, an exercise room, a 27-foot Boston whaler available for charter, as well as that Edgartown godsend—a dedicated off-street parking lot. The Hob Knob also rents out two nearby homes—a four-bedroom renovated schoolhouse and a five-bedroom house with a private pool—with daily housekeeping, concierge service, and access to the Hob Knob spa.

Rebuilt and reopened after a fire in 2001 leveled it, the Mansion House is again the anchor of the Vineyard Haven business district. The archival photos hanging in the hallways were used as guides for its current Victorian-style appearance, and the guest rooms' authentic period decorations—old-fashioned furniture and fabric patterns—illustrate the care taken with this restoration. The 40 rooms are island-small—although rates are comparatively low for the Vineyard—and many have small private balconies, wet bars, flat-screen TVs, gas fireplaces, and original works by Martha's Vineyard artists. Ask for a fourth-floor suite on the harbor side for the best views. The hotel's best feature is its Cupola Deck, a spacious outdoor terrace at the top of the hotel with unmatched harbor views to the north, and clapboard houses surrounded by white picket fences and the church steeples of town to the south and west. Suited for wellness seekers, Mansion House has a two-level gym and an indoor pool (rare for the Vineyard); the Moshup's Mud wrap at the full-service spa uses clay from the native Gay Head Wampanoag tribe mixed with wildflower honey from Edgartown's Katama Farm; and the casual restaurant, Zephrus, serves healthy preparations of food that's been locally caught, raised, or grown.

Set on two and a half wooded acres, this romantic retreat is great for couples. (Children aren't forbidden, but they're discouraged; and there's a strict double-occupancy rule, so if you are bringing the kiddies, be prepared to rent an additional room.) This place is decidedly not for fans of contemporary furnishings: It's antiques all the way—sometimes to the point of mustiness. And while the inn now has Wi-Fi, which is, at least, a nod to the 21st century, a slight overall refreshing would be a good idea. Three buildings house 14 large rooms with four-poster beds, wood-burning fireplaces, whirlpools, and balconies; room 1 has a hot tub on a private screened porch and several have a private entrance. The main 1908 classic Craftsman-style bungalow once housed guests of the estate's owner, John Herbert Ware, a Chicago grain merchant. Carriage-house rooms are more secluded, but for absolute solitude, ask for the private cottage with its own deck and garage. Fuel up with hearty egg and cheese strata or cheddar French toast in the two dining rooms, or continental breakfast in bed (just don't expect a mimosa, as Vineyard Haven is a dry town).

On 11 acres bordering South Beach near Katama Bay, the Winnetu caters to families in a way that most of the more stylish inns on the island do not. It also has a pleasantly lazy pace—even the front desk shuts down at 6 pm (8 on Fridays). The 50 suites and studios all have washer-dryers and kitchens—which can be stocked for you in advance—as well as decks or patios facing the ocean. (Ask for an upper floor, as the view is somewhat distant: Due to strict zoning laws, the property is set back about 250 yards from the water.) There's also a private cottage for those seeking more privacy. A 2007 refurbishment introduced a bolder, cleaner look, with lots of blond wood and blue-and-white printed fabrics. The main draw here, though, is the variety of family activities: There's outdoor ping-pong, foosball, a putting green, canoeing and kayaking excursions on Poucha Pond, daily lighthouse and dune trips, tea and cookies every afternoon, and Wednesday-night clambakes. A wellness center, opened in summer 2006, hosts classes, excursions, and spa treatments. A three-mile bike path and ferry shuttle service link the resort to Edgartown. At Lure, the excellent and surprisingly ambitious restaurant, chef Mark Goldberg (formerly of Mistral in Boston) focuses on local, sustainable ingredients, such as Katama Bay oysters, fresh-caught fish, and produce grown just down the road at Edgartown's Farm Institute. The Winnetu is surrounded by the affiliated Matakesett Properties and Tennis Club, a collection of single-family homes and townhouses available for weekly rental—convenient for families with kids, as long as you don't mind the 1970s ski-chalet look.

Open late May through late October.