Holiday Homes in Southern Maryland

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Featured Holiday Homes in Southern Maryland

MOUNT VERNON RETREAT 🌸

9.8 out of 10, Exceptional, (125)
"This was a lovely property and in a great location! The owners were easy to work to with and made us feel very welcome. "
The price is NZ$417
includes taxes & fees
25 Aug - 26 Aug
MOUNT VERNON RETREAT 🌸

The Cottage

10.0 out of 10, Exceptional, (7)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is NZ$759
includes taxes & fees
18 Aug - 19 Aug
The Cottage

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

9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is NZ$676
includes taxes & fees
15 Sept - 16 Sept
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

10.0 out of 10, Exceptional, (1)
"Stay there while my new home was getting work done, house was clean, perfect size for my family. It’s 50 ft to an ice cream shop and laundry mat. Our hoist even included a gift card to the ice cream shop. Great communication and perfect stay for us, felt like home "
The price is NZ$846
includes taxes & fees
17 Aug - 18 Aug
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Welcoming 3-bedroom townhome with AC in Waldorf

The price is NZ$530
includes taxes & fees
25 Aug - 26 Aug
Welcoming 3-bedroom townhome with AC in Waldorf

Anne & Fred's Leonardtown Home

9.4 out of 10, Exceptional, (3)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
The price is NZ$918
includes taxes & fees
18 Aug - 19 Aug
Anne & Fred's Leonardtown Home

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

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is NZ$650
includes taxes & fees
19 Aug - 20 Aug
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (2)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
The price is NZ$758
includes taxes & fees
28 Aug - 29 Aug
High River Bank with $1M Sunset View, 3 min to College

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

The price is NZ$564
includes taxes & fees
14 Sept - 15 Sept
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Spacious comfy Home in White Plains / Waldorf close to DC and National harbor

9.0 out of 10, Wonderful, (6)
"Nice location….enjoyed the stay."
The price is NZ$1,027
includes taxes & fees
18 Aug - 19 Aug
Spacious comfy Home in White Plains / Waldorf close to DC and National harbor

Charming Waterfront 3-bedroom house in Piney Point

The price is NZ$914
includes taxes & fees
14 Sept - 15 Sept
Charming Waterfront 3-bedroom house in Piney Point

Roomy 6 bedroom home in the heart of Solomons, MD

9.2 out of 10, Wonderful, (5)
"Stayed for business, completed our project and enjoyed some local eating spots. "
The price is NZ$1,159
includes taxes & fees
18 Aug - 19 Aug
Roomy 6 bedroom home in the heart of Solomons, MD

Charming 3-bedroom house with AC, WiFi just by MGM casino,close to Washington DC

The price is NZ$991
includes taxes & fees
17 Aug - 18 Aug
Charming 3-bedroom house with AC, WiFi just by MGM casino,close to Washington DC

Charming 4-House in central Waldorf

The price is NZ$1,350
includes taxes & fees
14 Sept - 15 Sept
Charming 4-House in central Waldorf

Charming 4-bedroom house with WiFi, fitness room in superb Waldorf

The price is NZ$3,100
includes taxes & fees
16 Aug - 17 Aug
Charming 4-bedroom house with WiFi, fitness room in superb Waldorf

Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger

10.0 out of 10, Exceptional, (13)
"Beautiful location . Close to all the things. Very convenient.. Felt like home!"
The price is NZ$534
includes taxes & fees
16 Aug - 17 Aug
Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

9.6 out of 10, Exceptional, (28)
"Nice and peaceful stay for a quick local getaway. "
The price is NZ$463
includes taxes & fees
17 Aug - 18 Aug
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is NZ$553
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

Historic charm with modern amenities

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is NZ$606
includes taxes & fees
17 Aug - 18 Aug
Historic charm with modern amenities

Dupont: Pet-friendly+Metro+42"Roku+Desk+FAST Wi-Fi

2.0 star property
9.2 out of 10, Wonderful, (5)
"Good location, steep steps going down if someone has mobility issues but once inside very comfortable. "
The price is NZ$425
includes taxes & fees
19 Aug - 20 Aug
Dupont: Pet-friendly+Metro+42"Roku+Desk+FAST Wi-Fi
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