Southampton Holiday Homes with Staff

We selected the 934 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

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Home spotlights in Southampton

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals.

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

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.


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

Explore the 934 most perfect homes in our collection

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Most popular homes in Southampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Walcott

Walcott

  • 8 guests

  • 3 bedrooms

Bridgehampton, Southampton

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

The Little Sparrow

The Little Sparrow

  • 6 guests

  • 3 bedrooms

Shinnecock Hills, 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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