Southampton Holiday Homes with Staff

We selected the 916 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

Borne Back

Borne Back

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Just steps away from a private community beach, Borne Back was designed by its architect owner to provide a comfortable contemporary home in a perfectly quiet spot in the Hamptons. On a full acre plot next to Gardiner's Bay, it's surrounded by tall trees.

A Faithful Friend

A Faithful Friend

  • 10 guests

  • 6 bedrooms

Water Mill, Southampton

This home is nearly a hundred years old, but in terms of its luxury and comfort, it might as well be brand new. Once you’ve had a flick through the photos, you won’t be surprised to find out that it’s been featured in many design magazines.

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Built in 1800, Hitchbrook is a quintessential New England home. Surrounded by farmland and rolling hills, this home is a private getaway for those looking for a pastoral retreat.

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day.


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

Explore the 916 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

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Ahoy There

Ahoy There

  • 8 guests

  • 4 bedrooms

Shelter Island, The Hamptons

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Marble Muse

Marble Muse

  • 8 guests

  • 4 bedrooms

Water Mill, Southampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

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Check upcoming rates & availability for Southampton Holiday Homes with Staff


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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