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
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Southern Maryland vacation homes

Property grounds

1. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is AED 803
AED 1,372 total
includes taxes & fees
15 Sep - 16 Sep
Bright and airy waterfront getaway
Beach nearby

2. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is AED 393
AED 1,321 total
includes taxes & fees
24 Aug - 25 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
TV, fireplace

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, (6 reviews)
"Lovely!! Perfect for our family for a weekend adventure. Very fun spaces with everything you need. The morning stroll to see the sunrise over the water was divine! Thank you!"
United States
Kate J.
The price is AED 479
AED 1,006 total
includes taxes & fees
25 Aug - 26 Aug
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Exterior

4. MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (143 reviews)
"We had a fabulous stay. Clean, comfortable lodgings very close to Mount Vernon. Excellent host who aimed to please and definitely did! Would recommend and would stay there again!"
United States
Wendy K.
The price is AED 578
AED 1,050 total
includes taxes & fees
24 Aug - 25 Aug
MOUNT VERNON RETREAT 🌸
Outdoor dining

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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is AED 579
AED 1,787 total
includes taxes & fees
8 Sep - 9 Sep
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Pool

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AED 698
AED 1,882 total
includes taxes & fees
9 Sep - 10 Sep
Family Beach House: Spacious Deck, Grill & Views
Exterior

7. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,705 total
includes taxes & fees
18 Aug - 19 Aug
Plum Point Cottage #17
TV

8. Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Waldorf
The price is AED 1,028
AED 2,270 total
includes taxes & fees
18 Aug - 19 Aug
Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Coffee/tea maker, fridge, microwave, stovetop

9. Cozy Private Home | Near DC & Military Bases

Cozy Private Home | Near DC & Military Bases
Indian Head
The price is AED 455
AED 1,411 total
includes taxes & fees
23 Aug - 24 Aug
Cozy Private Home | Near DC & Military Bases
Terrace/patio

10. 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
10.0 out of 10, Exceptional, (1 review)
"Jut as described. Easy in easy out. Great for a few days with the family."
United States
Joshua T.
The price is AED 582
AED 1,333 total
includes taxes & fees
31 Aug - 1 Sep
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Interior

11. 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, (13 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AED 643
AED 1,417 total
includes taxes & fees
14 Sep - 15 Sep
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Smart TV, books

12. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AED 1,102
AED 2,593 total
includes taxes & fees
8 Sep - 9 Sep
4-BR Waterfront Turret Home
Interior

13. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
"Lovely place and neighborhood! "
United States
Marci M.
The price is AED 1,025
AED 2,003 total
includes taxes & fees
9 Sep - 10 Sep
Sunset Cottage - West River Access and Views!
Property grounds

14. 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, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is AED 1,697
AED 3,169 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Exterior

15. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (6 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 1,260
AED 2,931 total
includes taxes & fees
19 Aug - 20 Aug
Charming Waterfront 3-bedroom house in Piney Point
Interior

16. 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.
The price is AED 1,590
AED 4,222 total
includes taxes & fees
24 Aug - 25 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
6 bedrooms, desk, iron/ironing board, travel crib

17. Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room

Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
La Plata
9.6 out of 10, Exceptional, (4 reviews)
"Cane for a weekend of Faith and Fun and this is exactly what we needed. Comfortably suited our 10 needs and so much more. Peaceful, serene, beautiful animals, game room, so much to say. Hostess with the mostest!!!! Charity is a gem! My church family will be back!!!!!"
United States
Wadiya D.
The price is AED 1,756
AED 3,290 total
includes taxes & fees
16 Sep - 17 Sep
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
Smart TV, fireplace, table tennis, books

18. Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (138 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
The price is AED 1,253
AED 2,373 total
includes taxes & fees
23 Aug - 24 Aug
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Smart TV

19. 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
The price is AED 1,084
AED 2,249 total
includes taxes & fees
8 Sep - 9 Sep
3-bedroom house in Deale located on Bay many amenities and great views
TV, fireplace, video games, books

20. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AED 1,697
AED 3,637 total
includes taxes & fees
17 Sep - 18 Sep
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

10/10 Excellent
"The restaurant had excellent food. The concierge was really helpful getting us bus tour tickets."
Cheryl 4-night trip
Posted 2 hours ago
Gaylord National Resort & Convention Center

Explore a world of travel with Expedia