Destination guide

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 holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday 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 holiday home and experience everything that makes Southern Maryland a fun place to get away to. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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)
Natural features

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 centre:

  • 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)
How to get there

Travelling to and around Southern Maryland

The nearest airport is in Washington, DC (DCA-Ronald Reagan Washington National), located 28.7 mi (46.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into College Park, MD (CGS), which is 34 mi (54.7 km) away.

Catch a ride on the metro at Branch Ave. Station for ease of access to the rest of the city.

How many holiday rentals are available around Southern Maryland?

Our 2019 accommodation listings offer a large selection of 628 holiday lettings around Southern Maryland. From 298 Houses to 71 Cottages, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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

There are many lovely places to stay for a long holiday or just a weekend break in Southern Maryland. From HomeAway travellers, the popular destinations to visit are:

  • Washington DC: 2,103 holiday homes
  • Virginia: 6,014 holiday homes
  • Le Droit Park: 253 holiday homes
  • Annapolis: 534 holiday homes
  • Old Town West: 71 holiday homes

HomeAway offers you the possibility to discover many other popular destinations in Southern Maryland! Please use our search bar to access the selection of self catering accommodations available in other popular destinations.

What are the main cities to discover in Southern Maryland?

Whether you are travelling solo or with family and friends, here are the cities in Southern Maryland with the largest selection of holiday lettings for a perfect city break:

  • Washington DC: 2,103 holiday lettings
  • Annapolis: 534 holiday lettings
  • Potomac: 2,239 holiday lettings
  • Stevensville: 621 holiday lettings
  • Ashburn: 246 holiday lettings

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

Can I find easy access holiday homes when travelling by plane to Southern Maryland?

Yes of course. Our owners offer a large selection of self catering accommodations near to airports. Airports with a large selection of self catering accommodations in Southern Maryland are:

  • Dulles International Airport (IAD): 275 self catering accommodations
  • Ronald Reagan Washington National Airport (DCA): 2,121 self catering accommodations
  • Leonardtown, MD (LTW-St. Marys County): 92 self catering accommodations

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

What are the most popular points of interest and landmarks to stay near in Southern Maryland?

HomeAway offers a large selection of holiday lettings near great places to visit in Southern Maryland. From HomeAway travellers, the top popular points of interest to stay for a holiday trip or just for a weekend are:

  • Perigeaux Vineyards and Winery: 90 holiday rentals
  • Walter E. Washington Convention Center: 1,137 holiday rentals
  • United States Navy Memorial: 2,135 holiday rentals
  • Cherry Hill Historic House and Farm: 2,135 holiday rentals
  • L. Ron Hubbard House: 2,144 holiday rentals

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

Explore destinations around Southern Maryland

Washington DC
2,103 holiday rentals
534 holiday rentals
2,239 holiday rentals
621 holiday rentals
246 holiday rentals
1,979 holiday rentals
1,897 holiday rentals
182 holiday rentals
51 holiday rentals
1,690 holiday rentals
34 holiday rentals
1,877 holiday rentals
327 holiday rentals
44 holiday rentals
106 holiday rentals
Royal Oak
76 holiday rentals
115 holiday rentals
100 holiday rentals
West Falls Church
1,601 holiday rentals
119 holiday rentals