Southold Unique Homes

We selected the best homes worth renting in this location

Home spotlights

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.

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Mere steps from the beach, this four-bedroom farmhouse sleeps ten and is ideal for a large family getaway. Rustic it may be, but the interiors don’t skimp on style – white walls and pops of colour lend it a modern Scandinavian vibe.


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

Oyster Castle

Oyster Castle

  • 8 guests

  • 4 bedrooms

Westhampton Beach, Southampton

Saltbush

Saltbush

  • 7 guests

  • 4 bedrooms

Montauk, East Hampton

Vine Ripened

Vine Ripened

  • 6 guests

  • 3 bedrooms

Jamesport, North Fork

Blueberry Dream

Blueberry Dream

  • 6 guests

  • 4 bedrooms

Southampton, The Hamptons

Dragonfly Creek

Dragonfly Creek

  • 6 guests

  • 3 bedrooms

Bridgehampton, Southampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

Poolside Splendour

Poolside Splendour

  • 8 guests

  • 4 bedrooms

East Quogue, Southampton

Hamptons Spring

Hamptons Spring

  • 12 guests

  • 6 bedrooms

Shinnecock Hills, 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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