Southampton Holiday Homes with Staff

We selected the 924 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

An extra fee may apply

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Home spotlights in Southampton

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.

Sea Aster

Sea Aster

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, Nora Ephron and John Steinbeck.

Under The Ridge

Under The Ridge

  • 2 guests

  • 1 bedrooms

Gardiner, New York

This delightful cottage, nestled in the picturesque mountains of New York State’s famous Shawangunk Ridge, is an ideal spot for a cosy country escape. As the last property before the entrance to a protected nature reserve, this home offers unmatched tranquillity and proximity to nature.


We selected the top 3% holiday homes in Southampton Holiday Homes with Staff

Explore the 924 most perfect homes in our collection

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Most popular homes in Southampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

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Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Southampton, The Hamptons, Suffolk County, New York, United States? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Southampton, The Hamptons, Suffolk County, New York, United States as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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