Book Luxury Holiday Rentals in Maryland

Award-winning homes from £98

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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.

The Mesmerised Voyager

The Mesmerised Voyager

  • 6 guests

  • 3 bedrooms

Astoria, Queens

The Mesmerised Voyager is located in Astoria, Queens, and we’ll tell you why this home is perfect. Not only is Astoria super well-connected to the city, it’s also got great international restaurants (Greek food is a must) and practically no tourists at all.

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.

Creative's Corner

Creative's Corner

  • 4 guests

  • 2 bedrooms

Annapolis, Maryland

Combining chic, laid-back living with an air of sophistication, this apartment in the heart of West Street, Annapolis, is a stylish base from which to discover the local Arts District. A bright open space finished with elegant furnishings and accessories throughout presents the perfect place to balance work with play and a spot of relaxation too.


We selected the top 3% holiday homes in Maryland Holiday Rentals

Explore the 768 most perfect homes in our collection

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Most popular homes in Maryland

Worlds Away

Worlds Away

  • 6 guests

  • 2 bedrooms

Del Ray, Alexandria

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Cornwall, Orange County

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Creek Farm

Creek Farm

  • 10 guests

  • 5 bedrooms

East Quogue, Southampton

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

Sky-High Sanctuary

Sky-High Sanctuary

  • 6 guests

  • 2 bedrooms

Downtown, Baltimore

Washington Wanderlust

Washington Wanderlust

  • 6 guests

  • 2 bedrooms

Radnor - Fort Myer Heights, Fort Lesley J. McNair

Sutton Sunrise

Sutton Sunrise

  • 4 guests

  • 2 bedrooms

Sutton Place, Manhattan

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Maryland, United States. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Maryland, United States has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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