Holiday Homes in Southern Maryland

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Our top choices for Southern Maryland holiday homes

MOUNT VERNON RETREAT 🌸

MOUNT VERNON RETREAT 🌸
Alexandria
9.8 out of 10, Exceptional, (132 reviews)
"Everything was as advertised and very clean"
United States
Jamie
The price is €229
includes taxes & fees
15 May - 16 May
MOUNT VERNON RETREAT 🌸

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)
"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 €270
includes taxes & fees
30 Apr - 1 May
Walk to Beach! King Bed & Free Beach Passes

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 €383
includes taxes & fees
27 May - 28 May
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (2 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 €424
includes taxes & fees
6 May - 7 May
Sunset Cottage - West River Access and Views!

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, (33 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is €345
includes taxes & fees
30 Apr - 1 May
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is €456
includes taxes & fees
30 Apr - 1 May
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is €392
includes taxes & fees
30 Apr - 1 May
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (19 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 €303
includes taxes & fees
30 Apr - 1 May
Bright and airy waterfront getaway

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (7 reviews)
"This property was super gorgeous and spacious so we were able to relax. Guests had more than enough space and didn’t feel like they were on top of each other sleeping wise! We were able to just have dinner and feel safe! The owner answered any questions we had within 15 minutes, which was super helpful! "
United States
khaddija j.
The price is €647
includes taxes & fees
7 May - 8 May
Tranquil Modern Farmhouse

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

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, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
Peaceful Waterfront Retreat for Bird Lovers- Close to DC

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, (8 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is €334
includes taxes & fees
12 May - 13 May
Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €890
includes taxes & fees
30 Apr - 1 May
4-BR Waterfront Turret Home

3-Bedroom Beach Home w/ Backyard

3-Bedroom Beach Home w/ Backyard
North Beach
3-Bedroom Beach Home w/ Backyard

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (2 reviews)
"Beautifully and tastefully decorated, immaculately clean, completely stocked top to bottom! You can tell by all of the details that these hosts care about curating a perfect stay for their guests. "
United States
Leslie K.
The price is €502
includes taxes & fees
30 Apr - 1 May
Charming Waterfront 3-bedroom house in Piney Point

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME
Waldorf
Cozy 3-bedroom townhome in tranquil Waldorf. Your HOME away from HOME

Beach House w/TheaterRm, GameRm, Outdoor Shwr

Beach House w/TheaterRm, GameRm, Outdoor Shwr
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"This was a fantastic property and location for our stay in Lusby. The home is designed with families in mind, and there was plenty for everyone to do. The house is beautiful and in a quiet, residential community. You can walk to the beach less than two blocks away, and we found dozens of sharks teeth there! Josh was so helpful with advice throughout. We would definitely come again."
United States
Mollie O.
The price is €668
includes taxes & fees
25 May - 26 May
Beach House w/TheaterRm, GameRm, Outdoor Shwr

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, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €874
includes taxes & fees
30 Apr - 1 May
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Fall is here!!! Backyard retreat waiting for you and your guest.

Fall is here!!! Backyard retreat waiting for you and your guest.
Waldorf
6.0 out of 10, (2 reviews)
"The property is beautiful. Furniture is comfortable (beds, sofa, and chairs). Everything was clean when we checked in. The patio/deck was beautiful. We were able to sit out back and enjoy the evening although it was chilly because of the heating lamp. It was a nice weekend gateway for the ladies - we are already planning the next one! I highly recommend staying here."
United States
Jackie P.
The price is €353
includes taxes & fees
30 Apr - 1 May
Fall is here!!! Backyard retreat waiting for you and your guest.

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

Charming 4-bedroom house with WiFi, fitness room in superb Waldorf
Waldorf
The price is €1,627
includes taxes & fees
30 Apr - 1 May
Charming 4-bedroom house with WiFi, fitness room in superb Waldorf
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

Find out more about Southern Maryland

Southern Maryland Holiday Homes information

Number of reviews
380
Accommodation
291 Holiday Homes
Lowest Price
€229
Highest Price
€1,627

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