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Maryland Holiday Rentals

456 Maryland Holiday Rentals were found matching your criteria.

Select a city/town to narrow your vacation rental search or browse listings below:


Featured
$322 - $484 /night
$1574 - $2152 /week
Adorable Pet Friendly Family Home with Hot Tub

  75 reviews   Add to Favorites

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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Hidden Loft

  2 reviews   Add to Favorites

Home: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Accident, Maryland, United States


Featured
$1397 - $2066 /night
$5890 - $9387 /week
Beautiful Lakefront Home w/ Private Indoor Pool, Hot Tub ...

  42 reviews   Add to Favorites

Home: 8 Bedroom, 7.5 Bathroom, Sleeps 26
Location: Oakland, Maryland, United States


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Hermitage

Home: 4 Bedroom, 3.5 Bathroom, Sleeps 12
Location: Swanton, Maryland, United States


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Glamping-Cortina

  1 reviews   Add to Favorites

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, Maryland, United States


$250 - $375 /night
$1650 - $2400 /week
Contact 4 Specials! 3 Lvl Waterfrnt Twnhme Incl. Activities!

Home: 2 Bedroom, 2.5 Bathroom, Sleeps 6
Location: Essex, Maryland, United States


$650 - $650 /night
$4500 - $4500 /week
Lavish and Upscale Vacation Rental with view of the Marina!

Condo: 1 Bedroom, 1.5 Bathroom, Sleeps 6
Location: Annapolis, Maryland, United States


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Windy Acres

  2 reviews   Add to Favorites

Home: 3 Bedroom, 3 Bathroom, Sleeps 12
Location: Oakland, Maryland, United States


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Lazy Bear Lodge

  4 reviews   Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States


$90 - $90 /night
$575 - $575 /week
Waterfront cottage on the Upper Chesapeake Bay

Cottage: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: Elkton, Maryland, United States


$140 - $390 /night
$800 - $2700 /week
Cozy Bayside Home ~ Sleeps 10 ~ Dog friendly

Home: 3 Bedroom, 2 Bathroom, Sleeps 10
Location: Ocean City, Maryland, United States



$625 - $1175 /week
Cheeseburger in Paradise

Home: 3 Bedroom, 2 Bathroom, Sleeps 6
Location: Ocean City, Maryland, United States


$115 - $420 /night
$805 - $2940 /week
Towers 202

Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States


$155 - $400 /night
$1085 - $2800 /week
Ocean Hideaway 508

Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States


$110 - $215 /night
$770 - $1505 /week
Bradley On The Bay 318D

Condo: 2 Bedroom, 2 Bathroom, Sleeps 7
Location: Ocean City, Maryland, United States



$695 - $1595 /week
Capri 1710

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Ocean City, Maryland, United States



$500 - $795 /week
Ocean Colony 16 Apt

Apartment: 1 Bedroom, 1 Bathroom, Sleeps 4
Location: Ocean City, Maryland, United States


$155 - $260 /night
$1085 - $1820 /week
Surfwood 103

Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States



$795 - $2195 /week
Rainbow 1109

Condo: 2 Bedroom, 2 Bathroom, Sleeps 6
Location: Ocean City, Maryland, United States



$525 - $925 /week
Assateague Pointe 358

Home: 2 Bedroom, 1 Bathroom, Sleeps 6
Location: Berlin, Maryland, United States


$290 - $610 /night
$2030 - $4270 /week
Summer Place 8

Home: 4 Bedroom, 2.5 Bathroom, Sleeps 10
Location: Ocean City, Maryland, United States


$115 - $400 /night
$805 - $2800 /week
Towers 304

Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States


$155 - $420 /night
$1085 - $2940 /week
Ocean Hideaway 202

Condo: 2 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States


$150 - $175 /night
$625 - $2225 /week
Sandy Pause II B2

Home: 3 Bedroom, 2 Bathroom, Sleeps 8
Location: Ocean City, Maryland, United States



$450 - $895 /week
Bradley on the Bay 234H

Condo: 1 Bedroom, 1 Bathroom, Sleeps 6
Location: Ocean City, Maryland, United States


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