Where to stay around Southern Maryland, US?

Our 2019 property listings offer a large selection of 524 vacation rentals near Southern Maryland. From 236 Houses to 95 Condos/Apartments, 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 most popular destinations to visit are:

  • Washington, DC: 3,681 vacation rentals
  • Virginia: 8,150 vacation rentals
  • Annapolis: 531 vacation rentals
  • Eastern Market: 400 vacation rentals
  • Saint Michaels: 162 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: 3,681 rentals
  • Colonial Beach: 58 rentals
  • Alexandria: 3,125 rentals
  • Chesapeake Beach: 518 rentals
  • Stevensville: 632 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): 3,774 vacation rentals
  • Andrews Afb (ADW): 3,370 vacation rentals
  • Leonardtown, MD (LTW-St. Marys County): 80 vacation rentals

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

Head to the lively city of Southern Maryland

Enjoy the live music and other features of Southern Maryland. This city's sporting events, boating and shopping draw many visitors. Whether you're planning a family vacation, friends trip or romantic retreat, HomeAway has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Sightseeing in and around Southern Maryland

Do you want to find attractions to visit during your stay? Venture out of your vacation home and experience everything that makes Southern Maryland a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Six Flags America (27.4 mi / 44.1 km)
  • Running Hare Vineyard (5.9 mi / 9.5 km)
  • Maryland International Raceway (9.4 mi / 15.1 km)
  • White Plains Golf Course (11.3 mi / 18.2 km)
  • Perigeaux Vineyards and Winery (13.6 mi / 21.9 km)
  • Chesapeake Beach Water Park (16.4 mi / 26.4 km)

Exploring the natural landscape of Southern Maryland

Whether you're looking for fun outdoor activities or just want to take in the scenery, Southern Maryland is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city center:

  • Breezy Point Beach (13.9 mi / 22.4 km)
  • Jefferson Patterson Park and Museum (14.3 mi / 23.1 km)
  • Greenwell State Park (15 mi / 24.2 km)
  • Chapel Point State Park (15.9 mi / 25.5 km)
  • Annmarie Sculpture Garden and Arts Center (18.9 mi / 30.5 km)
  • St. Mary's River State Park (19.9 mi / 32 km)