Search Villas in Southern Maryland

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Villas in Southern Maryland and around

Leo Farm Villa - Beautiful Country Retreat by RedAwning

Leo Farm Villa - Beautiful Country Retreat by RedAwning

Leo Farm Villa - Beautiful Country Retreat 5 Bedroom Villa by RedAwning

3.0 star property
Leo Farm Villa - Beautiful Country Retreat 5 Bedroom Villa by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Southern Maryland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

9.8 out of 10, Exceptional, (124)
"We chose to celebrate our 10th wedding anniversary here for a quiet weekend away with our dog. The house provided everything we needed and the owners were great to deal with. Highly recommend!! "
Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Everything close by!"
The Blue Crab Beach House - Free beach passes

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (17)
"Beautiful and quiet in the fall. A great place for relaxing. Clean, great communication. End of the street with views of the bay. "
The price is €309
includes taxes & fees
26 Nov - 27 Nov
Soul Oasis - home on the Chesapeake Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your villa in Southern Maryland with Expedia?
Expedia makes it a breeze to find your dream villa in Southern Maryland. Taking the kids on holiday? Use our helpful filters to look for stays with amenities like free WiFi. If you have a certain budget, click on how much you want to spend and your preferred star rating. We’ll help you find the right place in tune with your taste and style.
How can I find cheap villas in Southern Maryland?
An excellent way to zero in on cheap villas in Southern Maryland is with Expedia’s handy filter tool. Narrow your search results by amenities, budget and star rating to discover unbeatable prices in only a few clicks.
What is there to do near my villa in Southern Maryland?
The most important accessory for your Southern Maryland adventure is a fabulous itinerary! Prince George’s Stadium, Belair Mansion and Allen Pond Park are among the most popular things to do if you’re on your way to Bowie. La Plata also lures visitors with its excellent attractions, such as Port Tobacco Players. Need more ideas for your to-do list? Stop by Hawthorne Country Club and College of Southern Maryland too.