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Southern Maryland, Maryland, United States of America

Southern Maryland holiday lettings

We found 581 holiday rentals — enter your dates for availability

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Find spaces that suit your style

Houses

View 367 Houses

Cabins

View 58 Cabins

Cottages

View 58 Cottages

Bungalows

View 58 Bungalows

Flats

View 150 Flats

Townhouses

View 28 Townhouses

Studios

View 102 Studios

Resorts

View 28 Resorts

Find the best place to stay — Southern Maryland

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
£ 206 avg/night
(84)

Beach cottage with a spectacular view!

Sleeps 12 · 4 Bedrooms · 4 Bathrooms
£ 328 avg/night
(26)

Waterfront riverhouse on a beautiful farm only 50 minutes from DC

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
£ 283 avg/night
(25)

Our Always Dreaming Cottage - The Bay At Your Back Steps

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
£ 265 avg/night
(50)

Waterfront Log Cabin with Million Dollar View, Shark's Teeth, Beautiful Bath

Sleeps 5 · 2 Bedrooms · 1 Bathroom
£ 210 avg/night
(114)

Waterfront Ridge Retreat Cabin on St Jeromes Creek

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
£ 157 avg/night
(9)

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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, Vrbo 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.

Activities

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.

Can I find a vacation rental around Southern Maryland?

Yes, our 2021 property listings offer a large selection of 581 vacation rentals near Southern Maryland. From 367 houses to 58 cabins, 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.