Where Is The Best Place To Stay On Martha’s Vineyard?

MV Beach

Where Is The Best Place To Stay On Martha’s Vineyard?

There are few places in the USA of more natural beauty than Martha’s Vineyard. To sit on one of its many pristine beaches listening to the crashing sound of the breaking waves is a soul enriching experience; to sail out of Vineyard Haven or Edgartown across the sparking, blue waters of Nantucket Sound washes weight from your shoulders; feasting on the locally-grown, organic farm-to-table fare reminds you that food should be an experience.

So that’s decided, next vacation you’re off to Martha’s Vineyard, right? But the question is Where To Stay?
Should you be “up-island”, “down-island”, in Vineyard Haven (or is that Tisbury?), in Edgartown (and if so “downtown”, “left fork” or “right fork”?), in Menemsha, on “Chappy” or perhaps Oak Bluffs and please, please tell me will I be able to get a drink! (don’t worry only one town on the island is still “dry”)

Well here, I hope, is a little help.

If you want to truly escape and avoid the summer crowds then head “up-island”. This constitutes the towns of West Tisbury, Chilmark and Aquinnah. The further west you get the more rural it becomes but also the more breathtaking the views. Aquinnah is very quiet but you will get stunning sunsets and a visit to Gay Head lighthouse and the “colored” cliffs is a must. There are also some absolutely stunning beaches “up-island” and many you can only access in summer if you’re actually staying in the town where the beach is located. So if you want to hang out at Lucy Vincent beach (or let it all hang out at the clothing optional section of that beach) then you need to be staying in Chilmark. Also if you head to Chilmark in March you’ll catch the Martha’s Vineyard film festival. Chilmark is the last truly “dry” town so no liquor stores nor alcohol served in restaurants. You can bring your own booze and the restaurants will happily provide mixers and glasses. The other “up-island” towns of Aquinnah and West Tisbury are “soggy” with wine and beer served in all restaurants. There really aren’t many restaurants “up island” but a couple that are there are excellent. In West Tisbury you can head to State Road restaurant and see if you have anyone famous sitting at the table next to you and in Aquinnah The Outermost Inn provides superb food and superb views.
If you’re looking for shops and restaurants you need to stay “down-island” but be aware that come July and August you’ll be sharing this part of the island with a whole lot of other folk. My tip – come in June, September or October. Everything is open, the weather is awesome and the madding crowds are some place else.

“Down-island” comprises Vineyard Haven (aka Tisbury if you’re a town official, aka VH if you’re a local), Oak Bluffs (aka party central) and Edgartown. If you’re after the quintessential New England harbor with picture perfect houses and picket fences then go no further than Edgartown. It’s also the best place to head if you want to increase your chances in life of bumping into David Letterman. It is home to beautiful South Beach, reachable via both “right fork” and “left fork” roads heading out of town. An even more beautiful beach is East Beach out on Chappaquiddick (Chappy”), which is reachable via a short car ferry from Edgartown. The two things you won’t get in Edgartown are parking and change. This place is absolutely mobbed in summer so car parking is tough and being the place “to be seen” as you wander the boutiques the prices here are a little north of extreme.

Heading along State Beach you’ll reach Oak Bluffs. This has a ferry service in summer only and is where the serious partying takes place. Home to the most pubs (Offshore Ale Company is both a pub and a brewery and is definitely worth stopping in – and the brewer is an avid Liverpool supporter, what more could you want!) this town can get very colorful in the summer and most colorful of all are the Gingerbread Houses that surround the town green. Both Edgartown and Oak Bluffs are “wet” towns so no need to worry about getting a drink to end (or start) your day. They both tend to shut up shop for the winter with most businesses closed.

Sitting between the lighthouses of West Chop and East Chop is Vineyard Haven. This is the true year round town with ferry service operating all year. The town wraps around the harbor and the lagoon creating water vistas from all over town. It’s also home to possibly two of the best restaurants on the island, Beach Road and Garde East, and to the best fresh seafood market at The Net Result and (insider tip coming up) most definitely the best lobster rolls at Grace Church, which are available Fridays only. It’s also home to the beautiful Tashmoo Town Beach. This beach is hard to get to but well worth the journey. You can relax on the beach looking across the inlet at “Chip Chop”, the stunning house where Diane Sawyer lives. Vineyard Haven is a “wet” town. Beer, wine and liquor are available in all restaurants.

Wherever you stay it is not essential to have a car so if the car ferries are already fully booked don’t despair. Unlike our neighbors across the water on the mainland in Cape Cod, Martha’s Vineyard has many options for transporting you around the island. Taxis are abundant, there are several bus loop routes with buses running every 15 minutes (and buses and taxis are not expensive, which makes them unique on Martha’s Vineyard!), the island is (fairly) flat(ish) so cycling is popular for getting around. For the more adventurous mopeds can be hired or there are several car hire companies on the island.

Lodging options on the island range from hotel/resorts, motels, inns, traditional Victorian B&Bs to modern boutique Bed and breakfasts. All have something different to offer and all will help you have a wonderful and memorable stay on this gorgeous island. Here are some Martha’s Vineyard hotels to check out.

Safe travels,