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4 night trip to Martha's Vineyard with my sister

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Toronto, Canada
Level Contributor
17 posts
4 night trip to Martha's Vineyard with my sister

Hi - I'm taking my sister on a trip to Martha's Vineyard in July. 4 or 5 nights. We are travelling from Toronto and do not want to rent a car. Any advice on where to stay (Oak Bluffs, Vineyard Haven or Edgartown? Which is easiest to get to from Ferry?), what to do while there and restaurants would be welcome.

We are in our 50s, want to just relax, read, walk a bit, enjoy good local food, do a bit of shopping, go for cocktails, relax on the beach (we are not big swimmers, hikers or nature freaks).

I'd like to stay in a lovely inn or resort (if those exist on MV) with 2 double beds in our room. Is there anything that is actually on the water? Water view? Spa services? Nice patios for drinks etc?

Any advice or info would be very welcome. Thanks!

Boston, MA
Destination Expert
for Cape Cod, Massachusetts, Martha's Vineyard
Level Contributor
5,410 posts
131 reviews
1. Re: 4 night trip to Martha's Vineyard with my sister

There are lots of places that fit your description.

Depending on which ferry you take, you will either dock in Oak Bluffs or Vineyard Haven, these 2 along with Edgartown are the 3 main towns. You do not need a car on the island as there is very easy, inexpensive public transportation as well as taxis. Edgartown is my favorite, a beautiful old whaling town with a pretty harbor & lighthouse. Check out the Kelly House:


and the Harbor View:


annapolis, md
Destination Expert
for Annapolis, Maryland
Level Contributor
1,132 posts
275 reviews
2. Re: 4 night trip to Martha's Vineyard with my sister

Even though Martha's Vineyard is a small island the towns are very diverse. I definitely vote for Edgartown as the place to establish my base from. It's such a classic NE experience with more sophistication and elegance than the other places.

Be sure to visit Gay Head LIght and the Aquinnah Cliffs for stunning views. We also loved going to Menemsha, which is a tiny fishing village. It's just a perfect example of a typical waterman's spot. We used to come by boat and stay in the adjacent Salt Pond often being the only vessel around. The stars were incredible.

Level Contributor
1,270 posts
24 reviews
3. Re: 4 night trip to Martha's Vineyard with my sister

I agree. Focus on Edgartown, and I have no doubt you will find something. I would not be terribly fixated on having a water view from your hotel. It is possible, but you might get something better if you skip the water view. However, well south of Edgartown the Winnetu is a hotel with a sweeping waterview, but it is not in town. I've never stayed there.

Level Contributor
131 posts
4. Re: 4 night trip to Martha's Vineyard with my sister

You can also take the Pied Piper ferry from Falmouth, which docks right in Edgartown. If you've decided to stay in Edgartown, this is the best ferry for you.

Martha's Vineyard
Destination Expert
for Martha's Vineyard
Level Contributor
846 posts
118 reviews
5. Re: 4 night trip to Martha's Vineyard with my sister

The ferry boats generally dock in either Oak Bluffs or Vineyard Haven, with the only exception being the Pied Piper as the poster above mentioned. Each of the three 'down-island' towns, Oak Bluffs, Vineyard Haven and Edgartown, have wonderful and unique shops. Try to visit each town for the shopping. The only two places you can stay and see the water, in Edgartown, are the Harborside and the Harborview. They both have a pool, and the Fuller Street beach is a short walking distance away. I wouldn't recommend the Winnetu, as it is out away from town, with no shops or restaurants (other than Lure, at the hotel) close by.

6. Re: 4 night trip to Martha's Vineyard with my sister

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