We recently spent two weeks on Martha's Vineyard, and stayed at three different high-end properties. The Outermost was by far our favorite. It's one of those places where, if you looked at it piece by piece, you might be tempted to dwell on its shortcomings. But the whole package is marvellous.
Yes, there is no air conditioning. We were there during a period of exceptional heat and humidity, so this was not ideal. Yes, the rooms are looking a bit past their prime and could benefit from renovation. Yes, our bed could have used a new mattress. Yes, the price was high -- we paid $350/night (which includes a sumptuous breakfast), and that was not the most expensive room at the Outermost.
All that being said, we loved it. What makes the Outermost special is the ambience. The place exudes friendliness and down-home relaxation. It all starts with the inn keepers, Hugh and Jeannie Taylor, and their two adult children, Alexandra and Isaac. They are warm and friendly and welcoming. And mingling with other guests comes naturally, given the spacious and comfortable public areas at the Inn. We felt not so much customers as we did guests in the Taylors' country home.
The ground of the Outtermost are lovely, and guests have easy access to the beautiful, and very long, Aquinnah Beach.