A heron standing in a golden-hued wetland with a bird flying in the background.

Southern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (17 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$239 nightly
The price is $264
Nov 15 - Nov 16
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A lakeside view with chairs and a table, a rainbow, and trees.

2. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
$345 nightly
The price is $366
Nov 15 - Nov 16
Total with taxes and fees
Bright and airy waterfront getaway
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

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

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (9 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$281 nightly
The price is $298
Nov 16 - Nov 17
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
$287 nightly
The price is $309
Nov 15 - Nov 16
Total with taxes and fees
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

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

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
$292 nightly
The price is $310
Nov 15 - Nov 16
Total with taxes and fees
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A two-story house with a deck and a staircase leading to the upper floor.

6. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (151 reviews)
"What a beautiful and quaint little place to stay! So peaceful and the hosts were absolutely delightful! We will definitely be back!"
United States
Tiffany Z.
$255 nightly
The price is $293
Dec 4 - Dec 5
Total with taxes and fees
MOUNT VERNON RETREAT 🌸
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

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

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
$374 nightly
The price is $396
Nov 20 - Nov 21
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Three Adirondack chairs facing a beach with a clear view of the ocean.

8. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (10 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
$484 nightly
The price is $535
Nov 15 - Nov 16
Total with taxes and fees
Plum Point Cottage #14
Private kitchen

9. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
Just a getaway piece of property
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

10. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
$264 nightly
The price is $280
Dec 1 - Dec 2
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Fire pit (2)

11. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
$509 nightly
The price is $563
Nov 15 - Nov 16
Total with taxes and fees
Plum Point Cottage #15
A house with a yellow door and a window with a lamp outside.

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

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

13. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
$431 nightly
The price is $436
Dec 1 - Dec 2
Total with taxes and fees
Sunset Cottage - West River Access and Views!
Pool

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
$354 nightly
The price is $382
Dec 2 - Dec 3
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Fire pit (2)

15. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
Plum Point Cottage #17
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

16. 3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Amelia
$383 nightly
The price is $437
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom house in Deale located on Bay many amenities and great views
A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (8 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
$524 nightly
The price is $555
Nov 15 - Nov 16
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (41 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
$366 nightly
The price is $394
Nov 16 - Nov 17
Total with taxes and fees
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A spacious living room with a green sofa, glass coffee tables, and a fireplace. A staircase with a railing leads to an upper level.

19. Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
10.0 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay at this property and will definitely be back again!"
United States
Jeff and Nancy B.
$512 nightly
The price is $566
Nov 16 - Nov 17
Total with taxes and fees
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
A deck with outdoor furniture, a red door, and a house with windows.

20. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.4 out of 10, Exceptional, (3 reviews)
"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"
United States
Jenny A.
$314 nightly
The price is $358
Nov 15 - Nov 16
Total with taxes and fees
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
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.
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Top Southern Maryland Hotel Reviews

Best Western La Plata Inn

Best Western La Plata Inn

10/10 Excellent
"Great staff. Very customer oriented. Allowed me to check in early.easy access and close to many shopping opportunities"
Wesley 2-night trip
Posted 1 day ago
Best Western La Plata Inn

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 $264 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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