Stirling House Bed & Breakfast

The room was cute, cozy, and really comfortable. Clay was so friendly and gave us recommendations during our first time in Greenport. His food was amazing, especially the house rolls and strawberry jam, which I still keep thinking about. The breakfast and snacks alone would bring me back!

We only stayed two days, but it felt like a great little vacation, especially since it was our first B&B stay together since having kids. Clay was a lovely host, and his breakfasts were a treat, which makes sense since he’s a trained pastry chef. The house, bedrooms, and dining room were welcoming, clean, and tastefully decorated. The location is excellent for walking to places of interest. There’s also a bench across the front lawn where you can sit and watch the traffic on the water, with Shelter Island beyond. We’d highly recommend The Sterling House.

We hadn’t tried a bed and breakfast before, and my wife and I came away pleasantly surprised. It’s just a block from downtown Greenport, so getting around was easy. The hospitality was more than we expected, from the freshly baked pastries when we arrived to the self-serve coffee and snack area. There were sodas and snacks too, plus a bottle of Prosecco for us. Breakfast each morning was the highlight. The food was fresh and had the quality you’d expect from a top chef. I looked Clay up afterward and found out he’s a chef with a cookbook in bookstores. Thanks, Clay, for such a great stay. We hope to return soon.

We’ve stayed here twice now, and both visits were excellent. The house has a great view and is just down the street from downtown Greenport. Clay is friendly and knows a lot about the restaurants and wineries around town, and his breakfasts are delicious. We had to change our latest booking after we both came down with COVID. Clay was very kind about it and let us put the cancellation fee toward a future stay. I highly recommend The Stirling House. It’s the B&B we’d choose whenever we head to Greenport for a weekend.