The Hamptons Chalets

We selected the 47 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in The Hamptons

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

You don't even need to step out of this home to take in the view of Sam’s Creek and Mecox Bay, with the sea stretching out in the distance. At this cottage by the water, built up on stilts, you’ll be able to watch it all from the comfort of home.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

Zephyr Residence

Zephyr Residence

  • 10 guests

  • 5 bedrooms

Water Mill, Southampton

Stay in the heart of the heavenly Hamptons when you check in to this comfy home. It’s a short drive from the ocean (or ten minutes on the bikes provided by your host), and close to popular spots like Sag Harbor with its independent boutiques and quaint harbour.


We selected the top 3% holiday homes in The Hamptons Chalets

Explore the 47 most perfect homes in our collection

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Most popular homes in The Hamptons

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

Whale Watching

Whale Watching

  • 8 guests

  • 4 bedrooms

Sag Harbor, Southampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

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Frequently asked questions

A chalet in The Hamptons is the perfect accommodation for a cosy holiday. Find your dream one by browsing Plum Guide’s collection of homes. They 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 most charming chalets 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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