Maryland Holiday Homes with Staff

We selected the 768 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

0

Home spotlights in Maryland

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.

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.

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The summer retreat for Manhattan’s wealthy elite, the vibe of the Hamptons couldn’t be further from New York’s chaotic urban sprawl. And if you’re looking for the ultimate in serenity and tranquility, this idyllic beach house is for you.

Manhattan Lights

Manhattan Lights

  • 10 guests

  • 5 bedrooms

Midtown South, Manhattan

When it comes to location, this apartment in Midtown Manhattan is hard to beat. It's just a short walk away from Times Square, Broadway, MoMA and Central Park.


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

Explore the 768 most perfect homes in our collection

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Most popular homes in Maryland

The Reading Corner

The Reading Corner

  • 7 guests

  • 2 bedrooms

White Oak, Montgomery County

Cozy Town

Cozy Town

  • 2 guests

  • 1 bedrooms

Williamsburg, Brooklyn

The Captain's House

The Captain's House

  • 10 guests

  • 4 bedrooms

Jamesport, North Fork

Pine's Reach

Pine's Reach

  • 10 guests

  • 3 bedrooms

Walton Park, Chester

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

Bay Bliss

Bay Bliss

  • 6 guests

  • 4 bedrooms

Centerport, Huntington

Creative's Corner

Creative's Corner

  • 4 guests

  • 2 bedrooms

Annapolis, Maryland

Worlds Away

Worlds Away

  • 6 guests

  • 2 bedrooms

Del Ray, Alexandria

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Check upcoming rates & availability for Maryland Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Maryland? 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 Maryland 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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