Photo by Meg Faller

Holiday Homes in Southern Maryland

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Our top choices for Southern Maryland holiday homes

1. 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 AU$434
includes taxes & fees
12 Nov - 13 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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 AU$521
includes taxes & fees
10 Nov - 11 Nov
Bright and airy waterfront getaway

3. 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 AU$445
includes taxes & fees
15 Nov - 16 Nov
The Cozy Crab- Your Charming Haven in Lovely North 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 AU$397
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

5. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is AU$572
includes taxes & fees
2 Dec - 3 Dec
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

6. 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.
The price is AU$606
includes taxes & fees
1 Dec - 2 Dec
Sunset Cottage - West River Access and Views!

7. 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 AU$650
includes taxes & fees
2 Dec - 3 Dec
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

8. 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.
The price is AU$392
includes taxes & fees
18 Nov - 19 Nov
MOUNT VERNON RETREAT 🌸

9. 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 AU$570
includes taxes & fees
20 Nov - 21 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

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 AU$627
includes taxes & fees
13 Nov - 14 Nov
3-bedroom house in Deale located on Bay many amenities and great views

11. 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 AU$517
includes taxes & fees
9 Nov - 10 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

12. 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, (20 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AU$507
includes taxes & fees
10 Nov - 11 Nov
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

13. 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 traveller
The price is AU$1,124
includes taxes & fees
14 Nov - 15 Nov
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

14. 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 AU$970
includes taxes & fees
17 Nov - 18 Nov
4-BR Waterfront Turret Home

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, (9 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 AU$957
includes taxes & fees
14 Nov - 15 Nov
Charming Waterfront 3-bedroom house in Piney Point

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.
The price is AU$1,335
includes taxes & fees
10 Nov - 11 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

17. 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.
The price is AU$1,059
includes taxes & fees
16 Nov - 17 Nov
Tranquil Modern Farmhouse

18. 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 AU$1,168
includes taxes & fees
1 Dec - 2 Dec
2 Acre Oasis with Private Beach! Family and dog friendly!

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.
The price is AU$1,502
includes taxes & fees
8 Nov - 9 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub

20. 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 AU$991
includes taxes & fees
10 Nov - 11 Nov
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
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.

Learn more about Southern Maryland

Explore the family-friendly area of Southern Maryland—a scenic waterfront, sports teams and sights from Running Hare Vineyard to Budds Creek Motocross Park.

A white house with a red roof and a white lighthouse.
Photo by Meg Faller
Open Photo by Meg Faller

Top reviews in Southern Maryland

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