Southern Maryland, MD, USA

Southern Maryland, MD, USA

We found 502 vacation rentals — enter your dates for availability

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Find the best place to stay — Southern Maryland

Where to stay around Southern Maryland, US?

Our 2018 property listings offer a large selection of 502 vacation rentals near Southern Maryland. From 243 houses to 114 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Southern Maryland for a holiday or a weekend are on VRBO.

What are the most popular destinations to visit in Southern Maryland?

There are many lovely places to stay for a holiday trip or just for a weekend in Southern Maryland. From VRBO travelers, the top 5 most popular destinations to visit are:

  • Washington, DC: 1,770 vacation rentals
  • VA: 5,567 vacation rentals
  • Annapolis: 467 vacation rentals
  • Saint Michaels: 159 vacation rentals
  • Chesapeake Bay: 1,965 vacation rentals

And VRBO offers you the chance to discover many other popular destinations in Southern Maryland! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Southern Maryland?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Southern Maryland:

  • Washington, DC: 1,770 rentals
  • Annapolis: 467 rentals
  • Saint Michaels: 159 rentals
  • Alexandria: 1,648 rentals
  • Chesapeake Beach: 40 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Can I find easy-access vacation rentals when traveling by plane to Southern Maryland?

Yes of course. Our owners offer a large selection of vacation rentals near airports. The airports with a large selection of vacation rentals in Southern Maryland are:

  • Ronald Reagan Washington National Airport (DCA): 1,819 vacation rentals
  • Patuxent River NAS (NHK): 83 vacation rentals
  • Lee Airport (ANP): 561 vacation rentals

For other airports, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Southern Maryland?

VRBO offers a large selection of rentals near lovely places in Southern Maryland. From VRBO travelers, the top 5 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • United States Capitol: 1,810 rentals
  • Chesapeake Bay Bridge: 570 rentals
  • National Harbor: 1,765 rentals
  • Sandy Point State Park: 559 rentals
  • Breezy Point Beach: 181 rentals

But there are many other points of interest around Southern Maryland listed on VRBO where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.