Tucked away on the northwest corner is one of the Vineyard's best kept (and most affordable) secrets: the Menemsha Inn & Cottages, 14 acres (6 hectares) of gardens and woodlands overlooking the Vineyard Sound. Kids run free, playing tag and chasing wild turkeys in the sloping field that the 11 private cottages encircle. Families walk the short path down the hill to spend the day at Menemsha Beach or catch a shuttle to take advantage of free passes to Chilmark's exclusive Lucy Vincent and Squibnocket Beaches. Make sure to get out on the water, too: “Menemsha is a fishing mecca,” says inn owner Sarah Nixon. Sign on for a morning of in-shore fishing for striped bass and blue fish with 35-year Vineyard fishing veteran Captain Scott McDowell of North Shore Charters ($600, www.bassnblue.com).
Where to Play
Grab a bike and baby carrier from the inn and head to town to catch the ferry to Aquinnah, where you can cycle quiet two-laners at Lobsterville Beach or the hilly Gay Head Cliffs. Paddling Vineyard Sound can get choppy and rough, so take advantage of Book-a-Boat’s family special ($86, www.bookaboatmv.com) and head out for a couple of hours of bird-watching and exploring the coves of saltwater Menemsha Pond by kayak.
At Day's End
After a day on the dunes, join in on a classic New England clambake, complete with ocean views and pony rides. The inn's staff organizes evening fun (ask about a game of flashlight tag), while you sneak off to town for local lobster at Home Port Restaurant or live music on the Menemsha dock—if the stars are aligned, you might get an impromptu performance from summer local James Taylor or his sister Kate.
One-bedroom cottages are $2,200 a week; two-bedrooms, $3,700; www.menemshainn.com
Based on articles from National Geographic Adventure and updated by Greer Schott