Find Vacation Rentals in Chilmark

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Chilmark Information

Chilmark may have gained fame in recent years for playing host to the Obama family’s annual summer vacation, but this modest town on Martha’s Vineyard, off the southern coast of Massachusetts, dates back to 1660, well before the United States of America was even a country. Located on the western half of Martha’s Vineyard, the roughly 19 square miles of Chilmark boast just over 850 year-round residents, with population numbers swelling in the tourist-driven summer months. Chilmark is also home to Noman’s Island, an uninhabited piece of land off the northwest coast of Martha’s Vineyard used by the U.S. Navy as a practice bombing range until 1996. Now the island remains untouched as a fish and wildlife refuge, reflecting the pastoral and peaceful sentiment of Chilmark itself. Less busy than its neighboring Vineyard towns, Chilmark makes for a simple and picturesque New England getaway.

The town’s rolling hills and bucolic views are best observed by bicycle or foot. Rent a bike in nearby Tisbury or Edgartown and explore Chilmark’s North and South Streets, then follow State Road between Menemsha and Squibnocket Ponds through Aquinna. End at Gay Head, where you can tour its iconic lighthouse for a mere $5 fee. Menemsha Hills Reservation also boasts 211 acres of idyllic natural habitat, open to the public for everything from fishing to picnicking. Walk the Reservation’s 3 miles of trails, and even climb to the second highest point in Martha’s Vineyard, Prospect Hill. For movie buffs, Chilmark’s Menemsha Harbor may look familiar: it was the backdrop for Steven Spielberg’s famous film Jaws. Now Menemsha remains a small but active harbor for local fishermen, as well as residential and commercial boats. Visitors can even take a fishing charter boat from Menemsha to the nearby Elizabeth Islands through local outfitters such as Menemsha Blues Charters. If just a taste of Hollywood isn’t enough, visit during March for the famous Martha’s Vineyard Film Festival, which also hosts performance events throughout the summer months. If fishing isn’t your thing, enjoy the waters another way: via a stand up paddleboard (SUP). Aloha Paddle offers everything from your typical SUP rental to a “Paddle and Paella” event, where participants end a day of paddling with a BYOB paella beach cookout. And for the water weary, simply relax on Lucy Vincent Beach, or savor local fare at favorites such as The Menemsha Galley or the famous Chilmark Chocolates.

Martha’s Vineyard may be small, but that doesn’t mean there’s not a ton of things to do! From Chilmark, drive east about a half an hour to Oak Bluffs or Edgartown, two iconic towns on the island. Once a whaling center, Edgartown is the oldest settlement on the island and one of two Martha’s Vineyard towns where alcohol is sold, which makes it the scene of some of the island’s more exciting nightlife, as well as beautiful old mansions and boutiques. The town even maintains a 14-acre Japanese garden, Mytoi. Famous for its one-of-a-kind architecture, Oak Bluffs draws thousands of visitors per year with its “gingerbread houses,” playfully colorful residences and buildings. The town is also known for its Flying Horses Carousel, the oldest continuously running carousel in the country. From its family-friendly arcade, to its various shops and restaurants, Oak Bluffs is a lively vacation spot where anyone can feel like a kid again.

Known for its cozy bed and breakfasts, staying anywhere in Chilmark can make you feel at home. Chilmark’s main Bed and Breakfast is located near Menemsha Harbor, but Tripping.com can help you explore the town and find somewhere special to call your own during your island stay.

From Boston’s Logan International Airport, rent a car and drive down to Cape Cod, where you can catch a ferry to Martha’s Vineyard from Wood’s Hole, Falmouth, or Hyannis for a little over $16 round trip (and even cheaper for kids!). More limited ferry services are also available from Boston, New Bedford, New York City, New Jersey, and Rhode Island. There is also year-round scheduled service from nearby Massachusetts airports, as well as White Plains, New York and Providence, Rhode Island into Martha’s Vineyard Airport via Cape Air. Once on the island, there are various rental car centers available to the public, as well as taxi services. Martha’s Vineyard Regional Transit Authority also runs bus routes 7 days a week throughout the year, and these routes can take you virtually anywhere on the island. Bicycles and scooters are very popular amongst visitors, too! Local outfitters such as Sun’n’Fun Rentals or Martha’s Bike Rentals can help you find exactly what you’re looking for.