A white house with a red roof and a white lighthouse.

Southern Maryland Vacation Rentals

Dates

November 2026

December 2026

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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.

￥41,822 total

includes taxes & fees

Nov 10 - Nov 11

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

North Beach

Johanna S.

￥47,336 total

includes taxes & fees

Nov 12 - Nov 13

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.

￥49,053 total

includes taxes & fees

Nov 10 - Nov 11

4. Just a getaway piece of property

Mechanicsville

David L.

￥34,457 total

includes taxes & fees

Nov 15 - Nov 16

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

5. Bright and airy waterfront getaway

Benedict

George

￥57,956 total

includes taxes & fees

Nov 10 - Nov 11

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

6. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

￥46,701 total

includes taxes & fees

Nov 10 - Nov 11

A house with a yellow door and a window with a lamp outside.

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

Deale

Maude H.

￥50,262 total

includes taxes & fees

Nov 15 - Nov 16

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

Chesapeak beach

Ben W.

￥60,593 total

includes taxes & fees

Dec 2 - Dec 3

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

9. Sunset Cottage - West River Access and Views!

Shady Side

Michelle H.

￥68,834 total

includes taxes & fees

Dec 1 - Dec 2

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

10. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

￥37,276 total

includes taxes & fees

Nov 16 - Nov 17

A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

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

North Beach

Sarah

￥72,415 total

includes taxes & fees

Nov 16 - Nov 17

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

12. MOUNT VERNON RETREAT 🌸

Alexandria

Tiffany Z.

￥43,105 total

includes taxes & fees

Nov 16 - Nov 17

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

13. 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

￥69,195 total

includes taxes & fees

Nov 13 - Nov 14

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

14. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

Shady Side

"the house was clean and fully stocked with all linens. there are some staples in the refrigerator and cabinets. All cookware and eatery are provided. there is only one grocery store in the area, so plan ahead. Fast food is not readily available. Nick responded quickly and thoroughly to all messages, that was great. It's a quiet neighborhood. It was the perfect place for a family and pet. we will return"

Jenny A.

￥56,729 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Leonardtown

Christy C.

￥87,999 total

includes taxes & fees

Nov 10 - Nov 11

A spacious living room with a green sofa, glass coffee tables, and a fireplace. A staircase with a railing leads to an upper level.

16. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

port tobacco

Jeff and Nancy B.

￥100,896 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Lexington Park

Andrea B.

￥56,571 total

includes taxes & fees

Nov 11 - Nov 12

18. Plum Point Cottage #14

Huntingtown

Yonnick H.

￥84,864 total

includes taxes & fees

Nov 10 - Nov 11

19. Plum Point Cottage #15

Maryland

￥89,396 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Point Lookout

sandi c.

￥65,578 total

includes taxes & fees

Dec 1 - Dec 2

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Find vacation rentals that suit your style

Top Southern Maryland Hotel Reviews

A modern hotel lobby with a reception desk, a large red abstract mural, a herringbone wood floor, a seating area with a sofa and chairs, and a bar with a high counter.

The Rose Gaming Resort

Dumfries

10/10 Excellent

Michael

A living room with a sofa, armchairs, a coffee table, and a bookshelf.

Archer Hotel Old Town Alexandria

Old Town Alexandria

10/10 Excellent

Richard

A wooden double door with glass panels, a porch with a railing, and a view of the outdoors.

Swanendele Inn at St. Mary's Maryland

Ridge

10/10 Excellent

dina

A modern kitchen with a large island, bar stools, and a wine rack.

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

A spacious lobby with a reception desk, seating area, and large windows.

The Inn at Leonardtown, an Ascend Collection Hotel

Leonardtown

10/10 Excellent

Edward

A hot tub in a grassy area with a building in the background.

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

An outdoor seating area with a fire pit, cushioned benches, and a modern design.

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Lexington Park

10/10 Excellent

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

A fire pit surrounded by wicker chairs and tables, with a brick patio and a building with large windows in the background.

Residence Inn by Marriott Upper Marlboro Joint Base Andrews

District Heights

10/10 Excellent

Jasmine

A Holiday Inn Express hotel with a modern facade, a prominent sign, and a well-lit entrance.

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

10/10 Excellent

Troy

A balcony with two wicker chairs and a small table, overlooking a cityscape and a body of water.

Gaylord National Resort & Convention Center

Fort Washington

10/10 Excellent

Yanli

A hotel lobby with a reception desk, a glass-top table with a bowl, potted plants, a vending machine, and a large window.

Springhill Suites by Marriott Prince Frederick

Prince Frederick

10/10 Excellent

laura

A modern hotel lobby with a sofa, chairs, a fireplace, and a large window.

Comfort Inn & Suites Lexington Park near Pax River

Lexington Park

10/10 Excellent

I just joined a colleague at this hotel after his selection, but it was a great experience, and this was a first-time, three night stay. First, for a budget hotel, they have an acceptable gym with one ea. tread, elliptical, bike plus a multi-station; they also advertise (though I didn't get to it) an agreement with a local regular gym should you be interested. Well located for fast foods, and perfect for quick access to NAS Pax Gate 2. Rooms were large, internet worked, breakfast was pretty huge...

Anonymous traveler

A hotel lobby with a bar area, seating arrangements, and a television screen.

Hampton Inn Waldorf

Waldorf

10/10 Excellent

Mikayla

A modern living room with a fireplace, two sofas, a coffee table, and a bookshelf.

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

Suitland

10/10 Excellent

Natasha

Find out more about Southern Maryland

Vacation Apartments in Southern Maryland

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Southern Maryland Vacation Rentals

Change your mind

Treat yourself

Be picky

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. Bright and airy waterfront getaway

6. Soul Oasis - home on the Chesapeake Bay

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

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

9. Sunset Cottage - West River Access and Views!

10. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

12. MOUNT VERNON RETREAT 🌸

13. 3-bedroom house in Deale located on Bay many amenities and great views

14. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

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

16. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

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

18. Plum Point Cottage #14

19. Plum Point Cottage #15

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

Find vacation rentals that suit your style

Top Southern Maryland Hotel Reviews

The Rose Gaming Resort

10/10 Excellent

Find out more about Southern Maryland

Vacation Apartments in Southern Maryland

Explore a world of travel with Expedia