Monthly Rentals in Southold

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

We had a great stay at Todd’s house in Laughing Waters. The house is spacious, comfortable and well equipped. Some areas of the house could use a little sprucing up. Good set up for remote work. It is what is outside that makes Todd’s place special—proximity to the small beach nearby (a great spot for young children), the quiet neighborhood, the water view from the deck and the large yard and garden. Great place to walk/run, bike ride, kayak and swim. Quick drive to downtown Southold, Southold Seafood Market, Country View Farm Stand, the Southold dog park and several Vineyards. Over the course of our long stay we had a few minor issues and several questions. Todd responded quickly and in one instance sent his property manager over.

This house is a true gem! We were on the North Fork for our daughter's wedding - welcomed guests to the area from near and far and this beautiful spot allowed for the perfect launch point and gathering home base. There is an open floor plan so our extended family could gather and visit as we cooked and cleaned up in the kitchen. The back yard is a dream with the pool, hot tub and many recreational activities. My husband loved the outdoor grill set up! We rented the entire house, inclusive of the garden apartment, which was comfortable given the size of our group. Steve was terrific - warm, responsive and helpful. Our hosts even left a thoughtful gift of a Land's End bag, sweet note and some treats from the North Fork! The week was an absolute dream and we are grateful to have spent our time in this special space.

Great location, comfortable house! Conveniently located near lots of wineries and farm stands and within a quick drive or 20 minute walk to local beaches, this Airbnb is a great home base for a trip to the North Fork. The big fenced in yard was a plus for the dogs (and the kids!). We hope to return soon.