Holiday Houses in Maryland

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2,184 Holiday homes

Arrowhead #26

Oakland condo

3 bedrooms / 3 bathrooms / sleeps 10

from £112 / night

£781 / week

Cozy Cumberland Cabin in the Allegheny Mountains!

Cresaptown log cabin

1 bedroom / 1 bathroom / sleeps 4

2

Responds fast! avg. 30 minutes

from £67 / night

£469 / week

Waldins waterfront house with amazing views - Top of the Chesapeake

Charlestown house

3 bedrooms / 2 bathrooms / sleeps 8

3

Responds fast! avg. 53 minutes

from £246 / night

£1,717 / week

Best kept secret by the bay (Entire House)

Fishing Creek house

3 bedrooms / 2 bathrooms / sleeps 4

4

Responds fast! avg. 2 hours 54 minutes

from £152 / night

£913 / week

Waterfront Room Rentals 2 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 2 hours 46 minutes

from £90 / night

£535 / week

Surfcrest Condo Oceanblock Ocean City MD

Ocean City condo

1 bedroom / 1 bathroom / sleeps 6

4

Responds fast! avg. 1 hour 3 minutes

from £121 / night

£843 / week

Ski Harbor #37

McHenry house

3 bedrooms / 2 bathrooms / sleeps 8

from £102 / night

£712 / week

Wispering Ridge

Oakland house

2 bedrooms / 3 bathrooms / sleeps 6

4

from £102 / night

£712 / week

Hemlock Chalet

Oakland house

3 bedrooms / 2 bathrooms / sleeps 10

5

from £115 / night

£806 / week

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

Wittman log cabin

5 bedrooms / 5 bathrooms / sleeps 10

3

from £870 / night

£5,573 - £6,510 / week

Nice and very quiet ; Room 1.

Parkville house

1 bedroom / 1 bathroom / sleeps 1

from £26 / night

£182 / week

Steps to the Slopes

McHenry house

4 bedrooms / 4 bathrooms / sleeps 12

5

from £215 / night

£1,505 / week

Love Point Luxury Waterfront in Stevensville

Stevensville house

3 bedrooms / 4 bathrooms / sleeps 10

from £1,253 / night

£6,267 / week

Beautiful cabin in the woods w/private hot tub & game room, close to skiing

McHenry house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 1 hour 24 minutes

from £147 / night

£1,024 / week

Cambridge Colonial Home, Walk to Town & Waterfront

Cambridge house

3 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 30 minutes

from £214 / night

£1,498 / week

Panacea

McHenry house

6 bedrooms / 4 bathrooms / sleeps 13

11

from £124 / night

£868 / week

Waterfront Vacation Home with Private Beach

Trappe house

3 bedrooms / 3 bathrooms / sleeps 6

5

Responds fast! avg. 2 hours 46 minutes

from £295 / night

£1,766 / week

All Seasons

Swanton house

5 bedrooms / 3 bathrooms / sleeps 10

3

from £162 / night

£1,130 / week

Ski Harbor #21

McHenry house

3 bedrooms / 3 bathrooms / sleeps 8

2

from £102 / night

£712 / week

Owl Cabin

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 8

from £191 / night

£1,336 / week

Annapolis Crows Nest Cottage: Chesapeake Bay View

Annapolis villa

5 bedrooms / 3 bathrooms / sleeps 20

from £620 / night

£2,675 - £3,424 / week

Villages of Wisp #03 Lakeview Court

McHenry condo

2 bedrooms / 3 bathrooms / sleeps 8

from £144 / night

£1,005 / week

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

Bowie condo

2 bedrooms / 2 bathrooms / sleeps 6

1

Responds fast! avg. 10 minutes

from £134 / night

£714 / week

OCEANFRONT~Steps To Beach/Ocean/Pool~Uptown = PERFECT! Get Your 2020 Dates Now!

Ocean City condo

2 bedrooms / 2 bathrooms / sleeps 6

16

from £81 / night

£562 / week

Beautiful Day

McHenry house

5 bedrooms / 3 bathrooms / sleeps 14

3

from £124 / night

£868 / week

Spacious, waterfront home w/ pool table & shuffleboard - dogs OK!

Swanton house

4 bedrooms / 3 bathrooms / sleeps 10

1

Responds fast! avg. 1 hour 24 minutes

from £277 / night

£1,935 / week

Dreamer's Overlook

McHenry house

4 bedrooms / 3 bathrooms / sleeps 12

2

from £138 / night

£962 / week

Oceanfront condo w/ amazing views & beach access offers private pool, tennis!

Ocean City house

2 bedrooms / 2 bathrooms / sleeps 8

1

Responds fast! avg. 1 hour 36 minutes

from £79 / night

£550 / week

Tranquil Dreams

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

4

from £124 / night

£868 / week

Waterfront Room Rentals 1 with Private Beach

Trappe private room

1 bedroom / 1 bathroom / sleeps 2

1

Responds fast! avg. 2 hours 46 minutes

from £116 / night

£696 / week

Deep Creek Village #07

McHenry house

2 bedrooms / 2 bathrooms / sleeps 8

8

from £115 / night

£806 / week

AAH Chalet

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

13

from £172 / night

£1,199 / week

150/175 nt 3/4 bedrooms 40 miles from Washington 3 or 4 bedroom

Olney house

3 bedrooms / 2 bathrooms / sleeps 15

from £157 / night

£1,098 / week

Responds fast! avg. 1 hour 20 minutes

from £113 / night

£787 / week

Windy Acres

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 12

from £176 / night

£1,230 / week

Linwood

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

7

from £115 / night

£806 / week

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

Ocean City house

1 bedroom / 2 bathrooms / sleeps 4

1

Responds fast! avg. 1 hour 24 minutes

from £54 / night

£375 / week

Almost Heaven

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

from £124 / night

£868 / week

Top of the Slopes

McHenry condo

4 bedrooms / 3 bathrooms / sleeps 12

from £219 / night

£1,530 / week

Lakefront townhouse w/shared dock, shared pool & hot tub - lake & ski access

McHenry house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 24 minutes

from £98 / night

£687 / week

Viewing 40 of 2,184
rentals in Maryland

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