Discover a selection of 500 vacation rentals in Southern Maryland, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $138 per night, and houses and cabins are popular options for a stay in Southern Maryland. Either way, you'll find a rental for everyone's needs.
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, Vrbo 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.

How many vacation rentals are available around Southern Maryland, US?

Our 2020 property listings offer a large selection of 570 vacation rentals around Southern Maryland. From 363 house rentals to 61 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

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:

  • Northwest: 1,085 vacation rentals
  • Northeast: 544 vacation rentals
  • Southeast: 1,020 vacation rentals
  • Annapolis: 402 vacation rentals
  • Historic District: 93 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:

  • Annapolis: 402 rentals
  • District of Columbia: 1,805 rentals
  • Cambridge: 187 rentals
  • Colonial Beach: 60 rentals
  • St. Michaels: 142 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:

  • College Park, MD (CGS): 1,820 vacation rentals
  • Washington, DC (DCA-Ronald Reagan Washington National): 1,842 vacation rentals
  • Camp Springs, MD (ADW-Andrews Air Force Base): 1,749 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 most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Eastern Market: 31 rentals
  • National Mall: 1,068 rentals
  • King George: 82 rentals
  • Nationals Park: 1,818 rentals
  • United States Holocaust Memorial Museum: 1,866 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.

Explore destinations around Southern Maryland

402 vacation rentals
District of Columbia
1,805 vacation rentals
187 vacation rentals
Colonial Beach
60 vacation rentals
St. Michaels
142 vacation rentals
1,685 vacation rentals
1,666 vacation rentals
Silver Spring
1,638 vacation rentals
303 vacation rentals
1,539 vacation rentals
46 vacation rentals
498 vacation rentals
262 vacation rentals
118 vacation rentals
144 vacation rentals
55 vacation rentals
88 vacation rentals
1,834 vacation rentals
1,810 vacation rentals
North Beach
43 vacation rentals