Where to Stay
Rental Houses
My strong recommendation if possible is to get a rental house, given the hotels on the Vineyard are very expensive even in June, so you’ll get more bang for your buck with a house. Airbnb and VRBO are the best bet for any dates less than a full week.
If, however, you can make a full trip out of it and do a weeklong rental, I recommend going through an agent, as most properties are only available via agencies. I’ve sourced agents below (please feel free to mention I referred you).
Specializes in the Chilmark/Menemsha/Aquinnah area
Agent: Meg Bodnar
Hotels
Edgartown
10% discount with code WEDINEDGAR (yes, I asked if they would change it to BDAY instead of WED but they said they couldn't. NOT THAT I'M TRIGGERED BY IT!)
Chilmark/Menemsha
Aquinnah
Katama
The Winnetu (great resort for families, also has weeklong house rentals)
Oak Bluffs
Vineyard Haven
West Tisbury
(more remote but gets you access to the wonderful Lambert's Cove Beach)