An island icon since 1891, the historic Harbor View Hotel occupies a prized waterfront location at the end of Edgartown’s North Water Street and features unrivaled views of Edgartown Lighthouse. The shingled property is an easy five-minute walk from downtown Edgartown, so guests can frolic at the beach by day and dine in town at night—all without driving, a rarity in Martha’s Vineyard. And the on-site amenities provide little reason to leave; the property features an outdoor pool, fitness center, yoga classes, Children’s Program and multiple dining venues, including Henry’s, an elegant gastro-pub, and Lighthouse Grill, a family-friendly venue with stunning views.

The 114 guest rooms, suites and cottages are incredibly varied, so selecting the proper room is crucial. The chic cottages are the newest and most luxurious accommodations thanks to a bevy of amenities; the one-, two- and three- bedroom options include a washer/dryer, outdoor shower, kitchenette, fireplace and many feature a private porch. The historic main building is home to a number of accommodations that are ideal for those who want water views and don’t require the space of a cottage, and basic hotel rooms are located in the Governor Mayhew building.

With its cheerful interiors featuring mismatched furniture, pastel-colored wallpapers and cozy sitting nooks, the Hob Knob exudes personality. The rooms are outfitted in a hodgepodge design-scheme, with furnishings found at antiques fairs and flea markets. The loveliest of the rooms is on the third floor, and features a pink-and-yellow color palette, a skylight and a kitchenette. Despite its small size, the property features a small but functional gym and spa. One person’s drawback—the inn is on busy Main Street—is another’s delight: with the Hob Knob as your base, you’ll be able to navigate all of Edgartown’s shops on foot.

The Vineyard’s only Relais & Châteaux property is on a quiet street near the center of Edgartown. Guests stay in nineteen rooms furnished with French and English antiques and reproductions. The downstairs drawing rooms, with leather armchairs, chandeliers and oil paintings, exude a prim Edwardian air. It may be more formal than some of the other inns on the island (several people have used the word “precious”), but the Charlotte has a sense of humor, too: at the door, guests are greeted by Ozzie, a golden retriever wearing a tiny blue-and-white-striped tie.

Located in Katama, near Edgartown, the gray-shingled Winnetu looks toward South Beach, which can be reached via a short stroll through fragrant shrubs and pine trees. Guest rooms range from small studios to chic cottages, with spacious living rooms and many connecting options for families. The décor is simple, with white-painted wood furniture, plush sofas upholstered in blue-and-white fabrics, sand-colored carpets and original photographs by West Tisbury–based artist Marcia Smilack. Most units have a kitchenette and many have patios or terraces with thrilling ocean views.

What truly stands out at the Winnetu, however, is the graciousness of the staff, particularly when it comes to the smallest guests. The resort offers a long menu of complimentary children’s activities, including tennis lessons, visits to working farms, nature hikes, bike rides, volleyball and an oversize Alice in Wonderland-style chess board in the hotel’s courtyard. One couple I met, traveling with a baby and a toddler, told me that they had never felt as welcome as a family anywhere else.