I've been coming to Greenport yearly for the past 4 years, this is my 2nd time staying here. Such a great location as it is so easy to walk into town, no need to drive. Can walk to grocery, restaurants, ferry to shelter island, etc.
Nice to be able to go back to the room so easily, between whatever you are doing. We always find something to do, even just walking around town is a fun time.
I recommend planning a trip to Orient point state park during your stay (we go after we check out on the way home), great place to hike, enjoy nature, etc. Pack a lunch too! Especially early in the season its very empty and relaxing; dress for wind though.