Southern Maryland Vacation Rentals from $272: Search Short-Term Rentals

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Our top choices for Southern Maryland vacation rentals

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

1. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict

ed r.

$248 nightly

Nov 10 - Nov 11

Total with taxes and fees

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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

North Beach

Johanna S.

$276 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

3. The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach

James L.

$294 nightly

Nov 9 - Nov 10

Total with taxes and fees

4. Just a getaway piece of property

Mechanicsville

David L.

$199 nightly

Nov 15 - Nov 16

Total with taxes and fees

A waterfront view with a rocky shoreline, a pier extending into the water, and buildings along the shore.

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Deale

Maude H.

$281 nightly

Nov 15 - Nov 16

Total with taxes and fees

A lakeside view with chairs and a table, a rainbow, and trees.

6. Bright and airy waterfront getaway

Benedict

George

$345 nightly

Nov 10 - Nov 11

Total with taxes and fees

A two-story house with a deck and a staircase leading to the upper floor.

7. MOUNT VERNON RETREAT 🌸

Alexandria

Tiffany Z.

$237 nightly

Nov 16 - Nov 17

Total with taxes and fees

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

8. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$267 nightly

Nov 16 - Nov 17

Total with taxes and fees

9. Family Beach House: Spacious Deck, Grill & Views

Chesapeak beach

Ben W.

$369 nightly

Dec 2 - Dec 3

Total with taxes and fees

A modern kitchen with a large window, a dishwasher, and a ceiling fan.

10. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

$413 nightly

Dec 1 - Dec 2

Total with taxes and fees

An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

11. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

North Beach

Sarah

$423 nightly

Nov 16 - Nov 17

Total with taxes and fees

A deck with outdoor furniture, a red door, and a house with windows.

12. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

David S.

$315 nightly

Nov 9 - Nov 10

Total with taxes and fees

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

13. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

$375 nightly

Nov 20 - Nov 21

Total with taxes and fees

A living room with a sofa, coffee table, fireplace, and artwork on the wall.

14. 3-bedroom house in Deale located on Bay many amenities and great views

Deale

"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...

Amelia

$383 nightly

Nov 13 - Nov 14

Total with taxes and fees

Three Adirondack chairs facing a beach with a clear view of the ocean.

15. Plum Point Cottage #14

Huntingtown

Yonnick H.

$484 nightly

Nov 9 - Nov 10

Total with taxes and fees

A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

16. Anne & Fred`s Leonardtown Home W/ Arcade room!

Leonardtown

Christy C.

$524 nightly

Nov 9 - Nov 10

Total with taxes and fees

17. Plum Point Cottage #15

Maryland

$510 nightly

Nov 7 - Nov 8

Total with taxes and fees

A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

18. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Point Lookout

sandi c.

$374 nightly

Dec 1 - Dec 2

Total with taxes and fees

A covered patio with a view of a lake, furnished with chairs and a table.

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

Lexington Park

Andrea B.

$356 nightly

Nov 9 - Nov 10

Total with taxes and fees

20. Plum Point Cottage #17

Huntingtown

$409 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Top Southern Maryland Hotel Reviews

Econo Lodge Andrews Air Force Base

10/10 Excellent

"Nice place for stay , clean environment and quiet"

Island Inn & Suites, an Ascend Collection Hotel

10/10 Excellent

"The staff members were attentive and friendly. The nature and the view from the windows are wonderful. The room amenities need some cosmetic touch-ups and minor repairs, such as the blinds or a missing light bulb on the balcony. I would rate the breakfast as 3 out of 5."

Find out more about Southern Maryland

Everything you need to know about Southern Maryland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Maryland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Maryland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Maryland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Maryland. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southern Maryland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $272 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southern Maryland rentals

At Expedia, we put the best Southern Maryland vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Maryland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Check prices for these dates

Our top choices for Southern Maryland vacation rentals

1. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

3. The Cozy Crab- Your Charming Haven in Lovely North Beach!

4. Just a getaway piece of property

5. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

6. Bright and airy waterfront getaway

7. MOUNT VERNON RETREAT 🌸

8. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

9. Family Beach House: Spacious Deck, Grill & Views

10. Sunset Cottage - West River Access and Views!

11. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

12. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

13. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

14. 3-bedroom house in Deale located on Bay many amenities and great views

15. Plum Point Cottage #14

16. Anne & Fred`s Leonardtown Home W/ Arcade room!

17. Plum Point Cottage #15

18. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

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

20. Plum Point Cottage #17

Find vacation rentals that suit your style

Top Southern Maryland Hotel Reviews

Econo Lodge Andrews Air Force Base

Country Inn & Suites by Radisson, Camp Springs (Andrews Air Force Base), MD

Spark by Hilton Waldorf

Island Inn & Suites, an Ascend Collection Hotel

Red Roof Inn PLUS+ Washington DC - Oxon Hill

Days Inn by Wyndham Camp Springs/Andrews AFB DC Area

Find out more about Southern Maryland

Explore a world of travel with Expedia

Expedia's Latest Trends

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