I'm sorry to say that this inn is not worth the trip. Shelter Island is beautiful and we've stayed at several properties there over the years, none of which are particularly great. The main problem with the Ram's Head is, as my husband pointed out, you pay "luxury" prices and the inn is kind of crummy. I'm happy to pay $550 for a hotel suite, and will certainly pay much more than that if I'm staying somewhere nice, but the Ram's Head isn't. The grounds are beautiful, but the rooms are dingy and feel cheaply thrown together and badly in need of updating. We got three rooms and all had old, worn wall-to-wall carpeting. There was a 3" gap at the base of our door, so we could hear every footstep and conversation up and down the hall. In fact, facing our door was a bathroom shared between several rooms, which had a door that stuck; everyone who went in and out slammed the door to close it, day and night. The bathtub was beaten up and difficult to stand in because of its awkward shape, with a shower head that was much too low. The water pressure was very poor, and the temperature of the water was impossible to regulate. The hotel claims to have a/c, but little to no cool air came out of the registers all weekend and all 6 of us were too hot. The service in the restaurant is slow and housekeeping was unresponsive and ignored our "do not disturb" sign. In all, it felt like staying in a dorm room. I would have been satisfied had I paid $150 - $200, but we will never stay there again. Try the Harbor Front in Greenport; for the same price, you get what you pay for.
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC