Southern Maryland Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Southern Maryland holiday rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (50 reviews)
"Gorgeous. Host is very welcoming and available. Clear instructions, which are super helpful. Peaceful and stunning location. Thank you, Teresa!"
United States
Carver Z.
The price is HK$1,215
HK$2,467 total
includes taxes & fees
24 Jun - 25 Jun
Soul Oasis - home on the Chesapeake Bay
Exterior

1 bedroom in a basement with private Private bathroom with cool AC

1 bedroom in a basement with private Private bathroom with cool AC
Waldorf
The price is HK$415
HK$648 total
includes taxes & fees
1 Jun - 2 Jun
1 bedroom in a basement with private Private bathroom with cool AC
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is HK$1,332
HK$2,225 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (134 reviews)
"Everything was as advertised and very clean"
United States
Jamie
The price is HK$1,128
HK$2,064 total
includes taxes & fees
7 Jun - 8 Jun
MOUNT VERNON RETREAT 🌸
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (20 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is HK$675
HK$2,588 total
includes taxes & fees
1 Jun - 2 Jun
Walk to Beach! King Bed & Free Beach Passes
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,363
HK$2,828 total
includes taxes & fees
1 Jun - 2 Jun
Cottage Located on the Patuxent River!
Dining

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (14 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is HK$1,842
HK$3,539 total
includes taxes & fees
2 Jun - 3 Jun
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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 HK$2,414
HK$4,621 total
includes taxes & fees
8 Jun - 9 Jun
Charming Waterfront 3-bedroom house in Piney Point
Interior

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Lexington Park
10.0 out of 10, Exceptional, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is HK$1,450
HK$3,069 total
includes taxes & fees
1 Jun - 2 Jun
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River
Fridge, microwave, oven, stovetop

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is HK$1,587
HK$4,142 total
includes taxes & fees
1 Jun - 2 Jun
Anne & Fred`s Leonardtown Home W/ Arcade room!
6 bedrooms, free WiFi, bed sheets, wheelchair access

SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden

SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
Fort Washington
9.6 out of 10, Exceptional, (15 reviews)
"Had a wonderful stay, friends and family definitely enjoyed this nice house"
United States
Michael Y.
The price is HK$2,116
HK$5,225 total
includes taxes & fees
1 Jun - 2 Jun
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 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 HK$1,622
HK$2,758 total
includes taxes & fees
1 Jun - 2 Jun
Bright and airy waterfront getaway
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (4 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 HK$2,422
HK$4,446 total
includes taxes & fees
16 Jun - 17 Jun
Sunset Cottage - West River Access and Views!
Lobby

Riverfront Retreat-HotTubIDock|Fenced YardINear DC

Riverfront Retreat-HotTubIDock|Fenced YardINear DC
port tobacco
10.0 out of 10, Exceptional, (10 reviews)
"Our stay was lovely. Property , location and host were excellent Would definitely book again"
United States
Guðmundur Þór J.
Riverfront Retreat-HotTubIDock|Fenced YardINear DC
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$2,186
HK$4,922 total
includes taxes & fees
4 Jun - 5 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Private kitchen

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 HK$1,220
HK$3,374 total
includes taxes & fees
1 Jun - 2 Jun
3-bedroom house in Deale located on Bay many amenities and great views
Outdoor dining

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, (35 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is HK$2,785
HK$5,706 total
includes taxes & fees
14 Jun - 15 Jun
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is HK$2,077
HK$4,145 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Living area

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
The price is HK$1,760
HK$3,730 total
includes taxes & fees
4 Jun - 5 Jun
3-Bedroom Beach Home w/ Backyard
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

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Holiday Inn Express Washington DC East - Andrews AFB by IHG

2/10 Terrible
"I was very surprised at the horrible conditions of this hotel. I've stayed at Holiday Inn Express before it was a very nice experience. However, this DC East Andrew's AFB hotel is not good. The carpets in the hallways were smelly and dirty, and the room's carpeting was no different. The room smelled moldy, and the refrigerator did not work, so I had to call for maintenance. They fixed it immediately because I had to step out. But when I returned to the room to relax for the evening, I sat on the bed and it sank to one side. I checked it and noticed that the baseboard was broken. Needless to say, I was not pleased. I immediately contacted the front desk to request another room. Thankfully, they were able to get me another room. I'm already booked for two nights at this hotel, but I will be very reluctant to book at another IHG hotel again."
Janice 2-night trip
Posted 3 hours ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG

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