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Hotels in Edgartown
5 Hotels
The Hob Knob
128 Main Street, Upper Main Street & Tilton Way

Located centrally along a quaint stretch of Main Street, the Hob Knob is a welcoming bed & breakfast with a well-landscaped yard and wrap-around porch. Of course, in high-tourist season the prices reflect its status as a popular boutique -- but in a lot of ways, you do get what you pay for. Rooms are spacious and comfortable with Berber carpeting, luxurious European linens and bathrobes, lovely Classic American-cottage decor (though some rooms feel more tended to than others), and pretty bathrooms with marble sinks. Other highlights include the free organic, full-farm breakfast, and the fact that downtown Edgartown is a short walk away. This place isn't really geared toward families, though -- children under the age of seven aren't allowed, and teens would likely be bored by the lack of a pool on-site.

Vineyard Square Hotel & Suites
38 N Water St

Formerly the Colonial Inn (built in 1911), the Vineyard Square Hotel has reinvented itself as a modern-day hotel. It overlooks Edgartown harbor and the historical waterfront district, and extensive renovations over the years have brought about fresh, airy rooms, modern technology (free Wi-Fi, flat-screen TVs and iPod docks), and updated amenities (a salon, fitness center and popular on-site restaurant). The luxury suites offer the most high-end accommodations, with spacious kitchenettes and private decks. The most affordable rooms, though, are small and basic -- but even they feel fresh and show limited signs of the building's actual age.

Harbor View Hotel
131 North Water St

Built in 1891, The Harbor View Hotel was one of Edgartown's first luxury properties, and has an excellent location within walking distance of Main Street, but removed from the tourist season noise. The expansive 114-room property offers stunning harbor views, a seasonal outdoor pool, delicious on-site dining options, and beach-chic rooms with modern amenities such as free Wi-Fi and flat-screen TVs. There is no spa or fitness center on-site, which is common for Martha's Vineyard.

Winnetu Oceanside Resort
31 Dunes Rd, Rfd 270

The Winnetu, a massive property (for Martha's Vineyard) with gorgeous views and a location within a quick walk of the beach, doesn’t come cheaply. But families with kids will appreciate that the majority of activities are included in the room rates. The rooms are simple but comfortable, and refreshingly decorated in a colorful, coastal-cottage style. All rooms offer the amenities for cooking and dining in, but the on-site gourmet grill is a delicious option for dining out as well. Although it's a short drive (or free shuttle) to Edgartown's Main Street, the resort offers plenty to do on-site -- including yoga on the lawn, weekly seasonal clambakes, two outdoor tennis courts, a heated outdoor pool, and a putting green. The resort mainly caters to families, who often opt to book the more spacious cottages or multi-bedroom suites.

The Edgartown Inn
56 N Water St

This quaint inn is centered more around historical charm than modern amenities. It offers spacious but basic rooms donning a mix of Colonial and Queen-Anne furnishings, floral and toile wallpaper, and other antique touches that make you feel as if you're stepping back to 1798 (when the inn was originally built as a residence for whaling Captain Thomas Worth). The history of the inn is rich (John F. Kennedy stayed here while he was a state senator), but its history also means there are thin walls, creaky floors, and a lack of amenities. The central location, though, makes it an excellent base from which to explore the surrounding charming town and beaches. But plan to do so only during tourist season -- the inn is closed from November to early April.