Book Luxury Airbnb Alternatives in Southold

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.

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 Airbnb Alternatives

Explore the 3 most perfect homes in our collection

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Most popular homes

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Saltbush

Saltbush

  • 7 guests

  • 4 bedrooms

Montauk, East Hampton

Vine Ripened

Vine Ripened

  • 6 guests

  • 3 bedrooms

Jamesport, North Fork

Poolside Splendour

Poolside Splendour

  • 8 guests

  • 4 bedrooms

East Quogue, Southampton

Well & Happy

Well & Happy

  • 10 guests

  • 5 bedrooms

Southold, The Hamptons

Shutterly Charming

Shutterly Charming

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

The Fifties Barn

The Fifties Barn

  • 8 guests

  • 4 bedrooms

East Hampton, The Hamptons

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Frequently asked questions

Explore our collection of the most remarkable Airbnb Alternatives that Southold, The Hamptons, Suffolk County, New York, United States has to offer. Every home you'll find on Plum Guide comes fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Before being accepted into our collection, each home much pass a meticulous vetting process, culminating in a personal home visit from an independent Home Critic. Rent one of Plum Guide's luxury Southold Airbnb Alternatives, and enjoy a long or short stay to remember. Should you need any assistance with your booking, our friendly team of experts will be on hand to guide you through the process.

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