My wife and I stayed at Harbor Landing for two nights around Father’s Day. We had a small room with two twin beds. This worked great for a couple nights, but I wouldn’t recommend a small room like that for much longer than. What worked great was the location: right at the end of the main drag of Vineyard Haven (Main St).
So it’s a fairly bare bones place, but there is a good community kitchen, a nice roof deck, a common grill area, and a small lounge with a great TV. There was not much to the room itself. Only a couple outlets, which already had a lot of stuff plugged in. Window AC was functional but fairly noisy. Very small bathroom, but a great shower with fantastic water pressure.
We didn’t really see the staff much, but they did call us the day before arrival, to see which boat we were coming in on. And they let us check in 5 hours early, which was absolutely great. Check-in and check-out were easy, and the manager was great.
So I would recommend Harbor Landing if you want a great location and you don’t mind kind of roughing it. We enjoyed our stay a great deal.