Vacation Homes in Southern Maryland
Wander Wisely with exceptional service, 24/7 support
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Featured Vacation Homes in Southern Maryland

Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing

MOUNT VERNON RETREAT 🌸

Bright and airy waterfront getaway

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Heron's Nest - Back Creek Villa Covered Deck

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Private Chesapeake Bay Beach community…love to feel the sand between your toes?

The Blue Crab Beach House - Free beach passes 🦀

Beachside Oasis with Beach Passes & King Suite by A Haven Away

Saint Leonard Long Beach Beach House

Waterfront - renovated 3 bedrooms 2 full baths cottage
Top trending hotels in Southern Maryland

Gaylord National Resort & Convention Center
Vacation Rentals in Southern Maryland
What kind of vacation do you want in Southern Maryland? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Southern Maryland that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Southern Maryland, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Southern Maryland Vacation Homes essential information
Accommodation | 277 Vacation Homes |
|---|---|
Lowest Price | CA $101 |
Highest Price | CA $666 |
Popular accommodation | Stunning Chesapeake views from almost ever room, private 15 home community beach, fossils, 450 pier,crabbing,fishing, MOUNT VERNON RETREAT 🌸, Bright and airy waterfront getaway, 3-bedroom house in soothing Saint Leonard with AC for relaxing stays, Heron's Nest - Back Creek Villa Covered Deck, Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views, Private Chesapeake Bay Beach community…love to feel the sand between your toes?, The Blue Crab Beach House - Free beach passes 🦀, Beachside Oasis with Beach Passes & King Suite by A Haven Away, Saint Leonard Long Beach Beach House, Waterfront - renovated 3 bedrooms 2 full baths cottage, 3-bedroom house near DC |
More ways to wander Southern Maryland
Explore More Ways to Travel with Travelocity
- 3 Star Hotels in Claiborne
- Apartments in Addison Road Station
- Vacation Homes in Annapolis
- Bel Alton Hotels
- California Hotels
- Cottages in Callaway
- Camp Springs Hotels
- Cheltenham Hotels
- Chesapeake Beach Hotels
- Vacation Homes in Chesapeake Beach
- Cheverly Hotels
- Cottages in Claiborne
- Claiborne Hotels
- Extended Stay Hotels in Crofton
- Dunkirk Hotels
- Cabins in Eastern Shore
- Cottages in Eastern Shore
- Galesville Hotels
- Cottages in Greenbelt
- Hollywood Hotels
- Hyattsville Hotels
- Cottages in Indian Head
- Pet Friendly Hotels in Lexington Park
- Apartments in Maryland
- B&B in Maryland
- Cabins in Maryland
- Condos in Maryland
- Cottages in Maryland
- Extended Stay Hotels in Maryland
- Motels in Maryland
- Vacation Homes in Maryland
- Resorts in Maryland
- Villas in Maryland
- Mechanicsville Hotels
- Hotels near MGM National Harbor Casino
- Mount Rainier Hotels
- Condos in National Harbor
- National Harbor Hotels
- Newburg Hotels
- North Beach Hotels
- Oxon Hill Hotels
- Prince Frederick Hotels
- Saint Mary's City Hotels
- Cottages in Silver Spring
- Motels in Silver Spring
- Golf Resorts & in Southern Maryland
- Extended Stay Hotels in St. Leonard
- St. Leonard Hotels
- Hotels near St. Mary's College of Maryland
- Condos in St. Michaels
- Cottages in St. Michaels
- Pet Friendly Hotels in St. Michaels
- Suitland-Silver Hill Hotels
- Taylors Island Hotels
- Upper Marlboro Hotels
- Pet Friendly Hotels in Waldorf
- Waldorf Hotels
- Cottages in Washington
- Extended Stay Hotels in Washington
- Guest Houses in Washington
- All Inclusive Resorts & in Washington
- Beach Resorts & in Washington
- Casino Resorts & in Washington
- Gay Friendly Hotels in Washington
- Hotels with Early Check-in in Washington
- Hotels with Hot Tubs in Washington
- Washington Hotels
- Villas in Washington
- Advantage Rent-A-Car Rental Cars in Leonardtown
- Advantage Rent-A-Car Rental Cars in Prince Frederick
- Car rental National Harbor
- Car rental New Carrollton
- Car rental Upper Marlboro
- Car rental Waldorf
- Car rentals near Washington
- Drive-A-Matic Rental Cars in College Park
- First Car Rental Rental Cars in Shady Side
- Island Car Rentals Rental Cars in Leonardtown
- Island Car Rentals Rental Cars in Piney Point
- Midway Car Rental Rental Cars in Shady Side
- Movida Rent A Car Rental Cars in College Park
- Ok Mobility Rental Cars in Shady Side
- Sicily By Car Rental Cars in Bowie






