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

Search Vacation Homes in Southern Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Southern Maryland vacation homes

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

1. 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.
The price is AED 533
AED 1,191 total
includes taxes & fees
29 Oct - 30 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
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
The price is AED 845
AED 1,406 total
includes taxes & fees
12 Nov - 13 Nov
Bright and airy waterfront getaway
Living area

3. 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.
The price is AED 387
AED 1,263 total
includes taxes & fees
1 Nov - 2 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

4. 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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 512
AED 1,045 total
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

5. 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, (40 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
The price is AED 692
AED 1,863 total
includes taxes & fees
18 Nov - 19 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

6. 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.
The price is AED 569
AED 1,339 total
includes taxes & fees
2 Nov - 3 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A two-story house with a deck and a staircase leading to the upper floor.

7. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (150 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.
The price is AED 496
AED 942 total
includes taxes & fees
4 Nov - 5 Nov
MOUNT VERNON RETREAT 🌸
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

8. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 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.
The price is AED 735
AED 1,654 total
includes taxes & fees
4 Nov - 5 Nov
Sunset Cottage - West River Access and Views!
A deck with outdoor furniture, a red door, and a house with windows.

9. 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
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AED 628
AED 1,394 total
includes taxes & fees
18 Nov - 19 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

10. 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, (1 review)
"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
The price is AED 661
AED 1,608 total
includes taxes & fees
29 Oct - 30 Oct
3-bedroom house in Deale located on Bay many amenities and great views
A dining area with a wooden spiral staircase, a round table with chairs, a chandelier, and a clock on the wall.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (4 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
A pathway lined with trees and lights leading to a wooden building with a visible window.

12. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
The price is AED 1,697
AED 3,126 total
includes taxes & fees
29 Oct - 30 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious living room with a large sofa, a television, and a view of the ocean.

13. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AED 1,102
AED 2,697 total
includes taxes & fees
1 Nov - 2 Nov
4-BR Waterfront Turret Home
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

14. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
Tranquil Modern Farmhouse
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

15. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is AED 1,458
AED 3,114 total
includes taxes & fees
2 Nov - 3 Nov
2 Acre Oasis with Private Beach! Family and dog friendly!
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

16. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AED 698
AED 1,461 total
includes taxes & fees
3 Nov - 4 Nov
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A two-story house with a balcony, surrounded by trees and a wooden fence.

18. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is AED 1,131
AED 2,809 total
includes taxes & fees
30 Oct - 31 Oct
Charming Waterfront 3-bedroom house in Piney Point
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

19. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
Lakefront Cabin Near Solomons Island w/ Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Maryland Hotel Reviews

Hampton Inn & Suites National Harbor - Alexandria Area

Hampton Inn & Suites National Harbor - Alexandria Area

10/10 Excellent
"Spacious, kid friendly"
Jenae 2-night trip
Posted 22 hours ago
Hampton Inn & Suites National Harbor - Alexandria Area

Explore a world of travel with Expedia