Monthly Rentals in Southold

Loved Kenneth’s house. Perfect for my wife & I to get away and explore the north fork for a weekend. Great location Private house Clean Comfy Walkable to Kenneys beautiful beach sunset Drivable/uberable to key winery or Greenport locations if needed Exactly what we were looking for as a mini couples getaway Would highly recommend; likely a returning customer Kenneth was responsive and pleasant with clear instruction 5 stars!

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 fabulous stay at this adorable cottage. It had everything we needed and more. Great spaces indoors and out to hang out, walkable to one of our favorite wineries, other wineries & restaurants close by. Appreciated having a tandem kayak to use & explore Goose Creek. Enjoyed watching birds, including Baltimore oriole parents in a nest in the backyard. Would return again. Thank you!

we loved this place! Beach was so close walkable, the house was perfect for our stay. Host is super responsive. House had all the amenities we needed, beautifully tastefully decorated. We loved our stay