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Holiday Rentals in Maryland, United States

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
All Maryland Rentals
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Showing 998 of the 1,737 holiday rentals in Maryland.
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From
$2,119
Per Week
McHenry
7 Bedrooms, 5 Bathrooms, Sleeps 18
14 photos Details
Reviews (8) Make Enquiry
From
$2,801
Per Week
Swanton
5 Bedrooms, 4 Bathrooms, Sleeps 14
17 photos Details
Reviews (5) Make Enquiry
From
$3,578
Per Week
Oakland
4 Bedrooms, 4 Bathrooms, Sleeps 14
9 photos Details
Reviews (8) Make Enquiry
From
$1,601
Per Week
Oakland
5 Bedrooms, 5 Bathrooms, Sleeps 14
11 photos Details
Reviews (11) Make Enquiry
From
$6,373
Per Week
Oakland
9 Bedrooms, 9 Bathrooms, Sleeps 26
21 photos Details
Reviews (9) Make Enquiry
From
$2,492
Per Week
Swanton
5 Bedrooms, 5 Bathrooms, Sleeps 14
10 photos Details
Reviews (3) Make Enquiry
From
$1,720
Per Week
Oakland
5 Bedrooms, 3 Bathrooms, Sleeps 13
10 photos Details
Reviews (6) Make Enquiry
From
$1,268
Per Week
Swanton
4 Bedrooms, 3 Bathrooms, Sleeps 12
12 photos Details
Reviews (2) Make Enquiry
From
$1,976
Per Week
McHenry
6 Bedrooms, 4 Bathrooms, Sleeps 18
16 photos Details
Reviews (6) Make Enquiry
From
$1,213
Per Week
Swanton
4 Bedrooms, 4 Bathrooms, Sleeps 11
18 photos Details
Reviews (5) Make Enquiry
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From
$210
Per Night
Swanton
3 Bedrooms, 2 Bathrooms, Sleeps 8
8 photos Details
Reviews (2) Make Enquiry
From
$1,203
Per Week
McHenry
3 Bedrooms, 2 Bathrooms, Sleeps 8
29 photos Details
Reviews (6) Make Enquiry
From
$316
Per Night
Oakland
5 Bedrooms, 6 Bathrooms, Sleeps 12
11 photos Details
Reviews (1) Make Enquiry
From
$282
Per Night
Oakland
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (28) Make Enquiry
From
$2,242
Per Week
McHenry
5 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
Reviews (12) Make Enquiry
From
$220
Per Night
McHenry
3 Bedrooms, 3 Bathrooms, Sleeps 8
18 photos Details
Reviews (8) Make Enquiry
From
$96
Per Night
Oxon Hill
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Reviews (1) Make Enquiry
From
$453
Per Night
McHenry
4 Bedrooms, 3 Bathrooms, Sleeps 12
10 photos Details
Reviews (12) Make Enquiry
From
$339
Per Night
Oakland
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (12) Make Enquiry
From
$359
Per Night
Oakland
3 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Enquiry
From
$79
Per Night
Berlin
Studio, 1 Bathroom, Sleeps 4
14 photos Details
Reviews (7) Make Enquiry
From
$240
Per Night
Swanton
3 Bedrooms, 1 Bathroom, Sleeps 8
9 photos Details
Reviews (6) Make Enquiry
From
$272
Per Night
McHenry
3 Bedrooms, 2 Bathrooms, Sleeps 8
27 photos Details
Reviews (5) Make Enquiry
From
$506
Per Night
Frederick
6 Bedrooms, 5 Bathrooms, Sleeps 16
18 photos Details
Reviews (1) Make Enquiry
From
$128
Per Night
Sharpsburg
3 Bedrooms, 2 Bathrooms, Sleeps 7
8 photos Details
Reviews (23) Make Enquiry
From
$373
Per Night
Swanton
2 Bedrooms, 3 Bathrooms, Sleeps 9
19 photos Details
Reviews (22) Make Enquiry
From
$208
Per Night
Friendsville
2 Bedrooms, 1 Bathroom, Sleeps 7
28 photos Details
Reviews (10) Make Enquiry
From
$488
Per Night
Swanton
4 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
Reviews (26) Make Enquiry
From
$307
Per Night
McHenry
3 Bedrooms, 2 Bathrooms, Sleeps 6
2 photos Details
Reviews (1) Make Enquiry
From
$228
Per Night
Accident
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details
Reviews (1) Make Enquiry
From
$692
Per Night
Church Creek
3 Bedrooms, 2 Bathrooms, Sleeps 9
38 photos Details
Reviews (3) Make Enquiry
From
$133
Per Night
Oakland
2 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$213
Per Night
Adelphi
3 Bedrooms, 2 Bathrooms, Sleeps 10
17 photos Details
Reviews (1) Make Enquiry
From
$532
Per Night
Cambridge
6 Bedrooms, 3 Bathrooms, Sleeps 18
18 photos Details
Reviews (2) Make Enquiry
From
$117
Per Night
Waldorf
2 Bedrooms, 2 Bathrooms, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
$192
Per Night
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
21 photos Details
Reviews (2) Make Enquiry
From
$160
Per Night
Emmitsburg
3 Bedrooms, 1 Bathroom, Sleeps 5
4 photos Details
Reviews (2) Make Enquiry
From
$373
Per Night
Tilghman
1 Bedroom, 1 Bathroom, Sleeps 4
12 photos Details
Reviews (6) Make Enquiry
From
$399
Per Night
Swanton
4 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (3) Make Enquiry
From
$181
Per Night
Accident
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (1) Make Enquiry
From
$128
Per Night
Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Reviews (2) Make Enquiry
From
$106
Per Night
McHenry
3 Bedrooms, 3 Bathrooms, Sleeps 8
30 photos Details
Reviews (1) Make Enquiry
From
$1,278
Per Night
Cambridge
5 Bedrooms, 4 Bathrooms, Sleeps 18
38 photos Details
Reviews (2) Make Enquiry
From
$213
Per Night
Baltimore
5 Bedrooms, 5 Bathrooms, Sleeps 6
7 photos Details
Reviews (1) Make Enquiry
From
$128
Per Night
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
7 photos Details
Reviews (2) Make Enquiry
From
$266
Per Night
Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
17 photos Details
Reviews (3) Make Enquiry
From
$373
Per Night
Dames Quarter
6 Bedrooms, 7 Bathrooms, Sleeps 12
30 photos Details
Reviews (1) Make Enquiry
From
$266
Per Night
Swanton
3 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details
Reviews (1) Make Enquiry
From
$133
Per Night
Oakland
2 Bedrooms, 2 Bathrooms, Sleeps 7
22 photos Details
Reviews (1) Make Enquiry
From
$852
Per Night
Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
31 photos Details
Reviews (1) Make Enquiry
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Cabin and condo holidays in Maryland

Maryland is a state situated on the eastern seaboard of the United States of America. It is close in proximity to Virginia and West Virginia and these three states are steeped in history as prime battle zones during the American Civil War. As well as its rich history, however, Maryland also is blessed with some beautiful and tranquil locations which mean it’s a great destination for an American holiday.

Deep Creek Lake:

Situated in Garrett County on the western side of Maryland, the Deep Creek Lake area offers the appeal of mountains, forests, rivers and Maryland’s largest freshwater lake. It’s a fantastic destination for those who like activity holidays or who simply like the opportunity to get away from the frantic pace of city life!

The list of activities that can be enjoyed is impressive and includes hiking, rock climbing, whitewater kayaking, fishing, biking, and in the winter there’s the opportunity to experience ice fishing or to indulge in some skiing or snowboarding. At Bear Claw Snow Tubing Park, there’s even the opportunity for your family to experience “snow tubing”, courtesy of 800 foot tubing lanes. All you have to do is get on the tube and then brace yourself for the exciting and bumpy descent!

Beach frolics on the east coast:

If you’re looking for sights that will delight and thrill, then it’s not just the mountains to the west of Maryland that you should check out. Assateague Island on the east coast is famous for its feral horses and it’s a magic sight to see them galloping along the sands. The island is 37 miles long and can be accessed by bridge, meaning you can travel right to Assateague Island’s fabulous beaches by car. However, having got there, make sure you ditch your car and explore the island and its coastline by foot, canoe, or kayak.

As you’d expect, the island is popular with sunbathers and also offers pretty much the full range of beach-related activities that you’d expect to find at any top notch beach resort. It’s a great spot for indulging in some sea angling, casting a lure out into the breakers. Or you can swim, fly kites, or book onto a kayak trip to explore the island’s secluded nooks and crannies. It’s also worth taking a look at the Assateague Lighthouse which was built in 1867 and is open for public tours during the summer months at weekends.

A good base for exploring Maryland’s eastern reaches is the charming little town of Berlin, situated within close distance of Assateague Island and which is brimming with its own history and attractions. For those wanting the freedom that self catering provides, check out cottage or condo options.