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Rent Luxury Cottages in Southold

We selected the best homes worth renting in this location

Home spotlights in Southold

Well & Happy

Well & Happy

  • 10 guests

  • 5 bedrooms

Southold, The Hamptons

Just steps from the beach with views across Peconic Bay, this home brings ease and comfort to coastal living. Bikes are provided for exploring and it’s just a short drive to the restaurants and shops of Southold.

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

This home has everything a group of friends or family need for a comfortable stay in Long Island's North Fork. The space is spread across three floors and although the decor is a little dated, there's lots to like.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.

We selected the top 3% holiday homes in Southold Cottages

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Discover our curated collection of luxury holiday Cottages in Southold, The Hamptons, Suffolk County, New York, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Southold Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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