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Maryland Holiday Rentals

448 Maryland Holiday Rentals were found matching your criteria.

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


Featured
$1386 - $2066 /night
$5818 - $9387 /week
Beautiful Lakefront Home w/ Private Indoor Pool, Hot Tub ...

  41 reviews   Add to Favorites

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


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Wild Yough Villa

  49 reviews   Add to Favorites

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


Featured
$345 - $481 /night
$1479 - $2131 /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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Shenandoah

  37 reviews   Add to Favorites

Home: 5 Bedroom, 3.5 Bathroom, Sleeps 14
Location: Oakland, Maryland, United States


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Directly For Rates
Mystic Creek Villa

  2 reviews   Add to Favorites

Home: 5 Bedroom, 4.5 Bathroom, Sleeps 13
Location: Oakland, Maryland, United States


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Directly For Rates
Glamping-Stanley

Home: 1 Bedroom, 0 Bathroom, Sleeps 4
Location: Oakland, 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


Contact Owner
Directly For Rates
Glamping-Uzes

  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


$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



$600 - $1395 /week
Salty Sands II 103

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


$225 - $225 /night
$1575 - $1575 /week
Atlantic View 302

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


$210 - $785 /night
$1470 - $5495 /week
Harbour Island 301M

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


$200 - $200 /night
$950 - $2495 /week
4100 105

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



$725 - $1995 /week
Captains Bridge 4

Home: 3 Bedroom, 2 Bathroom, Sleeps 9
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



$500 - $795 /week
Ocean Colony 16 Apt

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


$250 - $720 /night
$1750 - $5040 /week
Surf Avenue 4

Home: 5 Bedroom, 2 Bathroom, Sleeps 12
Location: Ocean City, Maryland, United States


$69 - $259 /night
$483 - $1813 /week
Two Bedroom Condominium

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



$500 - $950 /week
Assateague Pointe 427

Home: 2 Bedroom, 1 Bathroom, Sleeps 7
Location: Berlin, Maryland, United States


$135 - $540 /night
$945 - $3780 /week
Diamond Beach 414

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


$85 - $260 /night
$595 - $1820 /week
Jamaican Sun 205

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


$80 - $110 /night
$560 - $770 /week
Barefoot Country 301

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


$115 - $220 /night
$805 - $1540 /week
Beachmark 3D

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


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