Where do you want to be?
Basically, the Island is divided into two different regions: “Down Island” (which includes Oak Bluffs Edgartown and Vineyard Haven) and “Up Island” (which includes West Tisbury, Chilmark, and Aquinnah).
What are you looking for in a vacation spot?
Up Island is quiet and peaceful, with not much activity, and awesome beaches.
Down Island is full of activity, awesome beaches, shops, restaurants, and entertainment.
And don’t forget about Chappaquiddick (which we affectionately call "Chappy"). It's the Island off the Island of Martha’s Vineyard. This is for people who Really want to get away! There are no stores on Chappy; just fantastic beaches and incredible fishing!
Island Towns
Now that we narrowed down what part of the Island you want to be in let’s take it town by town:
- Oak Bluffs is the number one vacation spot on Martha’s Vineyard. This is for many reasons. The town center and beaches are all in one area. In most cases it’s a small stroll or bike ride to both. There are large Victorian Homes around the town center of Oak Bluffs and the streets leading out of town to the beach. The Martha’s Vineyard Camp Meeting Association with it’s over 300 brightly colored gingerbread cottages is another popular destination.
- Edgartown closely follows Oak Bluffs in popularity. The town center is filled with Large Whaling Captains houses with rose covered white picket fences. The famous South Beach and Katama area have wonderful beach homes for rent.
- Vineyard Haven has a lively town main street with Owen Park and beach for a quick dip. Tashmoo and West Chop are some of the Islands nicest beaches. Centrally located and with the steamship authority’s main terminal, easy accessibility to all towns.
- West Tisbury: You’re starting to get into the woods of the Vineyard, Larger tracts of land and wonderful beaches like Lambert’s Cove and Long Point. Large Farms and Horse ranches are on this fertile land.
- Chilmark: You’ll notice the vast green pastures and stone walls of Allen’s Sheep Farm and other estates that expand out to the Ocean’s Edge. This is truly a beautiful place. One of the Island most famous beaches Lucy Vincent is at your disposal when you rent here!
- Aquinnah: You have entered paradise. If you are lucky enough to find a rental in the special town go for it! Located at the very end of the Island there is a small center with Restaurants and shops. Indian spiritual land and don’t forget to check out the beautifully colored clay cliffs and the lighthouse open daily for tours.
Finding Your Ideal Vacation Home
The unique character and features of each town make Martha's Vineyard one of the best places to stay!
For help finding your ideal vacation home, see Anchor Realty's homes for rent in Oak Bluffs, Edgartown, Vineyard Haven, and West Tisbury.
