Southold Unique Homes

We selected the best homes worth renting in this location

Home spotlights

Like a Whisper

Like a Whisper

  • 10 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.

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.

Oyster Castle

Oyster Castle

  • 8 guests

  • 4 bedrooms

Westhampton Beach, Southampton

An eco-friendly haven away from the world, you can see that the host’s focus on sustainability was instrumental in this home’s design. A solar powered saltwater pool, solar panels on the roof, and an electric car charging port make this Hamptons home a green getaway that doesn't compromise on style.


We selected the top 3% holiday homes in Southold Unique Homes

Explore the 3 most perfect homes in our collection

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Most popular homes

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Dragonfly Creek

Dragonfly Creek

  • 6 guests

  • 3 bedrooms

Bridgehampton, Southampton

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

Summer in the Hamptons

Summer in the Hamptons

  • 4 guests

  • 4 bedrooms

Hampton Bays, Southampton

A Court of Forest Green

A Court of Forest Green

  • 18 guests

  • 9 bedrooms

Noyack, Southampton

Water Mill Charm

Water Mill Charm

  • 4 guests

  • 2 bedrooms

Water Mill, Southampton

Purple China

Purple China

  • 8 guests

  • 4 bedrooms

Bridgehampton, Southampton

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Frequently asked questions

Plum guide offers a handpicked selection of the most unique homes in Southold, The Hamptons, Suffolk County, New York, United States. Our homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book a short or extended stay and secure the most unique home in Southold, The Hamptons, Suffolk County, New York, United States for your next getaway. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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