The Hamptons Five Bedroom Homes

We selected the 56 homes worth renting in this location

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Home spotlights in The Hamptons

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

If you need a base for a friendly get-together or a family reunion, then look no further than this abode in the heart of Westchester County. Thanks to the games room, gym and cinema room, there’s never a dull moment here – and that’s just what’s inside the home.

Woodberry

Woodberry

  • 12 guests

  • 6 bedrooms

Fort Greene, Brooklyn

A home as large, as elegant, and as characterful as Woodberry is too much to describe in this space. The photos give a good impression, but even then, it has to be experienced before you really understand how good this place is.

The Architect's Gallery

The Architect's Gallery

  • 10 guests

  • 5 bedrooms

Cairo, New York

This 150-year-old Hudson Valley farmhouse sits on 16 acres of land that includes an apple orchard. It’s an idyllic base for those seeking an escape to the peace of the Catskills – though the town of Windham is just a ten-minute drive.

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

Find your own slice of heaven in East Hampton with a stay in this impressive glasshouse. Surrounded by lush trees with beautiful views, this is the perfect setting for a restorative retreat or special family gathering.


We selected the top 3% holiday homes in The Hamptons Five Bedroom Homes

Explore the 56 most perfect homes in our collection

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Most popular homes in The Hamptons

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

The Great Harvest

The Great Harvest

  • 34 guests

  • 10 bedrooms

Coolbaugh Township, Monroe County

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

In the Heights

In the Heights

  • 12 guests

  • 5 bedrooms

Washington Heights, Manhattan

The Social Network

The Social Network

  • 20 guests

  • 7 bedrooms

Bedford-Stuyvesant, Brooklyn

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

Hamlet

Hamlet

  • 8 guests

  • 5 bedrooms

Miller Place, Brookhaven

River Song

River Song

  • 10 guests

  • 5 bedrooms

Dalton, Berkshire County

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Frequently asked questions

Spacious 5 bedroom homes in The Hamptons. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 5 bedroom homes that The Hamptons has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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