The Beach Plum Inn & Restaurant Rating: 4.0 Pearls
More refined than its sister property The Menemsha Inn, The Beach Plum offers comfortable rooms and suites with French-country style. The property is a beautiful, remote up-island spot overlooking Menemsha Harbor, the fishing village, and a lighthouse. While there are few on-site activities, guests can go next door to the Menemsha Inn to play tennis or hit the gym. Don't expect cell phone service here; part of the charm of sinking into a hammock on a private patio is not having any reception. Wi-Fi is available throughout the property for those who need to stay in touch, and an on-site restaurant -- while pricey -- is excellent.
Menemsha Inn Rating: 3.5 Pearls
The Menemsha Inn is a secluded and rustic option in the scenic up island area of Martha's Vineyard. A variety of rooms and cottages can suit different size groups, and all rooms have charming features like wood-burning fireplaces and screen porches. Freebies here include daily breakfast, (spotty) Wi-Fi, parking, and all the beach necessities like towels, chairs, and umbrellas. The inn is privately situated on 14 acres of gardens and fields overlooking the Menemsha Harbor, but is still close to nearby Lucy Vincent Beach.
Vineyard Square Hotel & Suites Rating: 4.0 Pearls
Overlooking Edgartown harbor and the historical waterfront district, the Vineyard Square Hotel has reinvented itself from its roots of the Colonial Inn, built in 1911. Extensive renovations over the years have turned this historical property into a modern-day hotel with fresh, airy rooms, modern technology (free Wi-Fi, flat-screen TVs and iPod docks), and updated amenities (a salon and spa, fitness center and popular on-site restaurant). The luxury suites offer the most high-end accommodations, with spacious kitchenettes and private decks.
Harbor View Hotel Rating: 3.5 Pearls
Built in 1891, The Harbor View Hotel & Resort has always held a grand presence in Edgartown. In the early days, it was one of the first luxury resorts for a town that had come into its own during the whaling industry boom. Today it's an expansive 139-room property offering 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.
Winnetu Oceanside Resort Rating: 4.0 Pearls
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.