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Uncle Matt,
The easiest place would be Oak Bluffs harbor and stay at the Wesley Hotel across the street. Or you could get a mooring in Edgartown harbor and stay at any number of B&B's right in town. Menemsha has a few slips, and the Menemsha Inn is right there.
During "the season" you're going to pay throug the nose, so just be aware. And you may not get a slip/mooring, so start looking now.
On the flip side, Clammer and Roger have a good idea. Pick your weekend just right and a night on the boat in Lagoon Pond, Tashmoo or Sengekontacket could be nice.
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