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.
Harbor View Hotel Rating: 3.5 Pearls
Though Harbor View Hotel & Resort no longer offers its dedicated kids' program, it still has multi-bedroom cottages with beach chic decor and full kitchens on offer, making sleeping arrangements for families easy. The outdoor pool is heated, and has poolside service in high season.
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 families and groups, and all rooms have charming features such as wood-burning fireplaces and screen porches. Freebies here include daily breakfast, (spotty) Wi-Fi, parking, and all the beach necessities such as 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.
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 selc-contained cottages can accommodate families, and 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.