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Holiday Homes in Southern Maryland

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Southern Maryland holiday 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 NZ$512
includes taxes & fees
12 Oct - 13 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A calm lake with kayaks, surrounded by dense green foliage.

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 NZ$631
includes taxes & fees
11 Oct - 12 Oct
Bright and airy waterfront getaway
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$591
includes taxes & fees
2 Nov - 3 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 NZ$460
includes taxes & fees
19 Oct - 20 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

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, (38 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$800
includes taxes & fees
3 Nov - 4 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

6. 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 NZ$826
includes taxes & fees
10 Nov - 11 Nov
Sunset Cottage - West River Access and Views!
Pool

7. 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)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$814
includes taxes & fees
9 Nov - 10 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

8. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is NZ$757
includes taxes & fees
12 Oct - 13 Oct
Rose Haven Coastal Cottage
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 NZ$475
includes taxes & fees
15 Oct - 16 Oct
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A modern kitchen with white cabinets, a wooden countertop, and a hanging pendant light.

10. Cozy Private Home | Near DC & Military Bases

Cozy Private Home | Near DC & Military Bases
Indian Head
10.0 out of 10, Exceptional, (1 review)
"The place was a great home base to relax in after a long day out. The massage chair was really helpful after a day of driving."
United States
Matt T.
Cozy Private Home | Near DC & Military Bases
A covered patio with a view of a lake, furnished with chairs and a table.

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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is NZ$730
includes taxes & fees
20 Oct - 21 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A spacious living room with a large sofa, a television, and a view of the ocean.

12. 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 NZ$1,280
includes taxes & fees
14 Oct - 15 Oct
4-BR Waterfront Turret Home
A two-story house with a balcony, surrounded by trees and a wooden fence.

13. 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 NZ$1,325
includes taxes & fees
30 Oct - 31 Oct
Charming Waterfront 3-bedroom house in Piney Point
A pathway lined with trees and lights leading to a wooden building with a visible window.

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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is NZ$1,505
includes taxes & fees
13 Oct - 14 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
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, (66 reviews)
"We were thrilled with this vacation spot! From the cleanliness of the home to the absolutely amazing views from every window and a beautiful sunset almost every day, we just loved it!"
United States
J B.
The price is NZ$1,468
includes taxes & fees
2 Nov - 3 Nov
2 Acre Oasis with Private Beach! Family and dog friendly!
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

16. 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 NZ$1,414
includes taxes & fees
20 Oct - 21 Oct
Tranquil Modern Farmhouse
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

17. 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, (3 reviews)
"We loved the quiet location, the privacy, and the dock out back. The house was stocked with everything we needed!"
United States
Nicholas L.
The price is NZ$1,719
includes taxes & fees
15 Oct - 16 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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.

18. 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 NZ$2,035
includes taxes & fees
15 Oct - 16 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub
A hallway with a wooden floor, a white wall, and a ceiling with a central light fixture. There is a door on the left and a mirror on the right.

19. 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 NZ$1,379
includes taxes & fees
14 Oct - 15 Oct
Huge Farmstay w/ Pool, Animals, Pond, Event Barn, & Clubhouse w/ Game Room
A modern kitchen with stainless steel appliances, wooden cabinets, and a central island.

20. Modern Spacious 5BR|3BA Prime DC|MGM|Gaylord

Modern Spacious 5BR|3BA Prime DC|MGM|Gaylord
Oxon Hill
The price is NZ$1,297
includes taxes & fees
12 Oct - 13 Oct
Modern Spacious 5BR|3BA Prime DC|MGM|Gaylord
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

Red Carpet Inn Indian Head

Red Carpet Inn Indian Head

8/10 Good
"Great location in proximity to Smallwood park for fishing tournament. Have adjacent land with outlets for parking boat. Room was clean looks like recently updated remodeled. Parking was well lit. Rooms and property were quiet. The only problem was windows have not been cleaned from outside and were extremely dirty. Great place for tournament fisherman to stay. There is gas station with 24hr grill down street as well as seafood place across the street. LaPlata was closest big town about 15 minutes away."
Joseph 7-night trip
Posted less than an hour ago
Red Carpet Inn Indian Head

Find out more about Southern Maryland

Southern Maryland Holiday Homes information

Number of reviews
277
Accommodation
302 Holiday Homes
Lowest Price
NZ$460
Highest Price
NZ$2,035

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