I ended up at the front desk of the Surfside Motel, nearly in tears, despondent after my dog and I were cornered by a very aggressive dog at the establishment where I was actually booked to stay (see my review of the Lorraine Parrish Bed and Breakfast in Vineyard Haven). "Oh you poor thing...of course we have a room for you and Didi," is what they said. They offered me coffee, gave Didi a dog biscuit and soothed my frazzled nerves. The room was spotlessly clean, in a great location, and the guests and staff who gathered in the office for the daily continental breakfast treated me as though they'd known me my whole life.
The hotel has a beautiful courtyard, ample off-street parking and (again) a wonderful staff. The price was very reasonable for the Vineyard in June/July. Some of the rooms have a view of the ocean, and I believe they all overlook the courtyard.
For a great experience on the Vineyard, with or without Fido, be sure to give the Surfside Motel a try!