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 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)
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 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)
How to get there

Traveling 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 center. 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.

Where to stay around Southern Maryland?

Our 2019 property listings offer a large selection of 610 vacation rentals near Southern Maryland. From 276 Houses to 70 Cottages, 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 HomeAway.

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 HomeAway travelers, the most popular destinations to visit are:

  • District of Columbia: 2,037 vacation rentals
  • Virginia: 6,463 vacation rentals
  • Annapolis: 525 vacation rentals
  • Saint Michaels: 126 vacation rentals
  • Alexandria: 1,863 vacation rentals

And HomeAway 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:

  • District of Columbia: 2,037 rentals
  • Annapolis: 525 rentals
  • Saint Michaels: 126 rentals
  • Alexandria: 1,863 rentals
  • Arlington: 1,950 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): 2,084 vacation rentals
  • Dulles International Airport (IAD): 258 vacation rentals
  • Cambridge, MD (CGE-Cambridge - Dorchester): 110 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?

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

  • Eastern Market: 376 rentals
  • United States Capitol: 2,069 rentals
  • National Mall (The Mall): 1,179 rentals
  • Kings Dominion: 42 rentals
  • Nationals Park: 2,054 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.

Explore destinations around Southern Maryland

District of Columbia
2,037 vacation rentals
525 vacation rentals
Saint Michaels
126 vacation rentals
1,863 vacation rentals
1,950 vacation rentals
Colonial Beach
62 vacation rentals
Chesapeake Beach
525 vacation rentals
Kent Island
648 vacation rentals
41 vacation rentals
1,845 vacation rentals
171 vacation rentals
Silver Spring
1,839 vacation rentals
314 vacation rentals
2,038 vacation rentals
North Beach
55 vacation rentals
223 vacation rentals
Falls Church
1,689 vacation rentals
Rock Hall
83 vacation rentals
45 vacation rentals
2,194 vacation rentals