A heron standing in a golden-hued wetland with a bird flying in the background.

Southern Maryland Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

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, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is HK$1,215
HK$2,426 total
includes taxes & fees
12 Aug - 13 Aug
Soul Oasis - home on the Chesapeake Bay
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
9.2 out of 10, Wonderful, (10 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$2,250 total
includes taxes & fees
27 Jul - 28 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
TV, fireplace

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, (1 review)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is HK$868
HK$1,934 total
includes taxes & fees
23 Jul - 24 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Terrace/patio

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
The price is HK$1,284
HK$2,795 total
includes taxes & fees
19 Jul - 20 Jul
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (52 reviews)
"The house was perfect for my family's needs for our stay. It was clean, quiet, and cozy. The owner was incredibly kind and gracious and incredibly helpful."
United States
Andrew C.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$896
HK$2,415 total
includes taxes & fees
20 Jul - 21 Jul
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
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, (17 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is HK$1,665
HK$3,318 total
includes taxes & fees
20 Jul - 21 Jul
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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$1,803
HK$2,949 total
includes taxes & fees
21 Jul - 22 Jul
Bright and airy waterfront getaway
Interior

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, (10 reviews)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is HK$1,372
HK$3,016 total
includes taxes & fees
21 Jul - 22 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Coffee/tea maker, fridge, microwave, oven

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

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 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$3,977 total
includes taxes & fees
19 Jul - 20 Jul
Anne & Fred`s Leonardtown Home W/ Arcade room!
Beach nearby

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)
"Although the house itself could use some maintenance, our stay was very comfortable. The rooms were spacious and it had all the amenities we needed. "
United States
Donovan B.
The price is HK$1,803
HK$3,990 total
includes taxes & fees
13 Aug - 14 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Smart TV, fireplace, ping pong, books

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, (134 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 HK$2,469
HK$4,845 total
includes taxes & fees
19 Jul - 20 Jul
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Fridge, microwave, oven, stovetop

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is HK$2,168
HK$5,590 total
includes taxes & fees
19 Jul - 20 Jul
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Pool

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 HK$2,187
HK$4,898 total
includes taxes & fees
28 Jul - 29 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
6 bedrooms, free WiFi, bed sheets

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, (16 reviews)
"Had a wonderful stay, friends and family definitely enjoyed this nice house"
United States
Michael Y.
The price is HK$2,229
HK$5,406 total
includes taxes & fees
20 Jul - 21 Jul
SuperLocation NationalHarbor near Gaylord MGM hotels- 6 bedrooms with BBQ Garden
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$2,688
HK$5,615 total
includes taxes & fees
2 Aug - 3 Aug
Charming Waterfront 3-bedroom house in Piney Point
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,136
HK$3,588 total
includes taxes & fees
17 Jul - 18 Jul
Plum Point Cottage #17
Interior

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 HK$2,775
HK$4,961 total
includes taxes & fees
3 Aug - 4 Aug
Sunset Cottage - West River Access and Views!
Smart TV, books

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 HK$3,135
HK$6,330 total
includes taxes & fees
22 Jul - 23 Jul
4-BR Waterfront Turret Home
Property grounds

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 HK$3,621
HK$6,746 total
includes taxes & fees
29 Jul - 30 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
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

10/10 Excellent
"My experience was great the woman that woman that prepared the breakfast area was great and the guy at the front desk was great"
Larry 1-night trip
Posted 3 hours ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG

Find out more about Southern Maryland

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