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Holiday Houses in Maryland

2,459 Holiday homes

Waldins waterfront house with amazing views - Top of the Chesapeake

Charlestown house

3

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £242 / night

£1,690 / week

Villages of Wisp #03 Lakeview Court

McHenry condo

  • Child friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

from £142 / night

£992 / week

Top of the Slopes

McHenry condo

  • Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £264 / night

£1,849 / week

Waterfront Room Rentals 2 with Private Beach

Trappe private room

1

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£529 / week

Steps to the Slopes

McHenry house

5

  • Child friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £237 / night

£1,658 / week

Best kept secret by the bay (Entire House)

Fishing Creek house

4

  • Air conditioning
  • •  Private garden
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from £149 / night

£895 / week

Renovated condo in convenient location -steps away from beach, shopping, dining

Ocean City house

1

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £48 / night

£332 / week

Beautiful Home in Nice Community with up to 7 bedrooms

Severn house

  • Child friendly
  • •  Air conditioning
  • •  Private garden
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £338 / night

£2,365 / week

Ski Harbor #21

McHenry house

2

  • Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £101 / night

£703 / week

Tall Castle

McHenry house

1

  • Child friendly
  • 4 bedrooms
  • 5 bathrooms
  • sleeps 12

from £178 / night

£1,245 / week

Dog-friendly condo with shared pool plus lake, canal, and golf course views

Ocean Pines house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £100 / night

£697 / week

Luxurious 2 BDR Condo in Bowie Town Center. Close to DC and Annapolis

Bowie condo

1

  • Nearest beach 30 km
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £132 / night

£705 / week

Simply Irresistible

McHenry house

3

  • Child friendly
  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

from £140 / night

£980 / week

Brookie Cottage on the Savage River

Swanton cottage

1

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £172 / night

£1,097 / week

Cozy Cumberland Cabin in the Allegheny Mountains!

Cresaptown log cabin

2

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £69 / night

£481 / week

Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview

Wittman log cabin

3

  • Beach / lakeside relaxation
  • •  Nearest beach 6 km
  • •  Swimming pool
  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £859 / night

£5,501 - £6,426 / week

Traditions on the Lake

McHenry house

  • Child friendly
  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from £255 / night

£1,781 / week

Waterfront Vacation Home with Private Beach

Trappe house

5

  • Beach / lakeside relaxation
  • •  Nearest beach 97 km
  • •  Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £291 / night

£1,743 / week

Deep Creek Village #07

McHenry house

8

  • Child friendly
  • •  Pet friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £114 / night

£795 / week

SUNsational

Swanton house

3

  • Child friendly
  • •  Pet friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £136 / night

£949 / week

Surfcrest Condo Oceanblock Ocean City MD

Ocean City condo

4

  • Child friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £119 / night

£829 / week

Linwood

Oakland house

7

  • Child friendly
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £114 / night

£795 / week

Oceanfront flat w/seasonal shared pool, sea views, and easy beach access

Ocean City house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £62 / night

£432 / week

Arrowhead #26

Oakland condo

  • Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £110 / night

£771 / week

Waterfront Room Rentals 1 with Private Beach

Trappe private room

1

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £115 / night

£687 / week

Bright Beginnings

McHenry condo

  • Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £136 / night

£949 / week

Deep Creek Village #12

McHenry house

4

  • Child friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

from £97 / night

£678 / week

Rocky Knoll II

McHenry house

6

  • Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £101 / night

£703 / week

Annapolis Home w/ Deck & Whitehall Bay Access

Cape Saint Claire house

  • Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £199 / night

£1,393 / week

Fifth floor, waterfront condo w/ shared pool - walk to restaurants

Ocean City house

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 1 bedroom
  • 2 bathrooms
  • sleeps 6

from £71 / night

£493 / week

AAH Chalet

Oakland house

13

  • Child friendly
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from £195 / night

£1,362 / week

Love Point Luxury Waterfront in Stevensville

Stevensville house

  • Beach / lakeside relaxation
  • •  Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 4 bathrooms
  • sleeps 10

from £1,228 / night

£6,140 / week

Ski Harbor #37

McHenry house

  • Child friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £101 / night

£703 / week

Townhouse in Historic Downtown Cumberland

Cumberland house

5

  • Child friendly
  • •  Air conditioning
  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

from £106 / night

£615 / week

5 BR - AWESOME lake views, pool, billiards, tennis & hot tub on Wisp Mountain!

McHenry house

3

  • Nearest beach 12 km
  • •  Swimming pool
  • •  Ski
  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from £220 / night

£1,536 - £2,589 / week

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

  • Beach / lakeside relaxation
  • •  Nearest beach 0.2 km
  • •  Child friendly
  • 5 bedrooms
  • 3 bathrooms
  • sleeps 20

from £348 / night

£2,641 - £5,281 / week

The Lodge at McHenry Cove Marina

McHenry house

7

  • Child friendly
  • 5 bedrooms
  • 4 bathrooms
  • sleeps 14

from £123 / night

£857 / week

Spacious condo w/partial ocean views, two balconies - walk to the beach

Ocean City house

1

  • Child friendly
  • •  Car not necessary
  • •  Air conditioning
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £61 / night

£426 / week

Pinnacle Perch

Swanton house

1

  • Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £123 / night

£857 / week

Wispering Ridge

Oakland house

4

  • Child friendly
  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £101 / night

£703 / week

Viewing 40 of 2,459
rentals in Maryland

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