It kills me to write this, because I don't want to give away our amazing secret place that we have loved going to, and hope to go back in the future. So let's keep this between us, ok? Ok, good.
My beau and I rented this place for 6 weeks last year, and for 8 weeks this year. I work at a national monthly travel magazine (let's call it Javel + Jisure), and I have been in luxury resorts and hotels all over the world, and, in general, I just can't wait to get back to our wonderful carriage house in G'port.
The house itself is so wonderfully decorated - clean, modern lines, gorgeous huge bathroom, amazing kitchen, awesome yard for grillin' and chillin.... we are even thinking of consulting the owner on how she renovated and decorated because her taste is awesome.
The house details: everything is user-friendly, and the heat and A/C work in seconds to heat or cool the place as you need it. There are wonderful amenities - from the nice olive oil to the fluffy white towels and bathrobes to the grilling implements. You can just show up and take it from there. Beautiful skylights that make sunny days awesome, and rainy days kinda mellow and fun, with the pitter-patter of the rain on the skylights. It is listed as a one bedroom but there's a day bed that I have always loved napping on which would be great for a single guest or a child.
The location is bananas. You don't need a car and it's an easy 7-minute walk from the Jitney or the train that stops right in town (and there's a parking spot right out front). You're right in Greenport, and of course near vineyards, beaches, lighthouses, farm stands, light houses, Shelter Island! So much to explore, and there are a bunch of good maps in her library section of the house of different hikes and bike rides.
The owner, Caroline, couldn't be nicer; she is available if you need her for any little thing. She is also a presence in the village of Greenport and can give you great ideas of all the side trips you can do from this home base.
I can't say enough that this is the house you want in Greenport, if you're looking for a cool place to stay on the East End. The hotels in town are not so great (think bachelorette groups) - this is the way to go!