Holiday Homes in Southern Maryland

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Featured Holiday Homes in Southern Maryland

The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"The place was inviting and beautiful. Will definitely stay there again."
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Relax on the spacious deck with a wicker sofa, cushioned chairs, and a hammock, perfect for unwinding in a serene atmosphere.

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

9.8 out of 10, Exceptional, (69)
"Property was exactly as advertised. Charming Farmhouse with plenty of space situated on a large property with a private beach. We even enjoyed some of the local restaurants, Captain Pat's Seafood and Tacos Haciendas."
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

Rising Sun Bay View Cottage
Waterfront Wildlife Retreat on the Patuxent River
Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (166)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (64)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Charming single-story house with a front porch and well-manicured lawn.

Bayfront Maryland Retreat w/ Deck, Near Beaches!

9.8 out of 10, Exceptional, (9)
"Lovely, serene, comfortable, waterfront home. Conveniently close to the essentials, restaurants, pier, beach, markets, and more. "
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (119)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Secluded River Front Cottage
Enjoy the serene view from this room's sliding glass door, leading to an outdoor space with a tree.

Secluded River Front Cottage

9.4 out of 10, Exceptional, (3)
"Nice property, with an amazing kitchen. There are beautiful sunsets and peaceful views of the water. A pleasent weekend get away"
Secluded River Front Cottage
Blocks to the Boardwalk!
Relax on the beach with access to the sandy shore and a scenic boardwalk.

Blocks to the Boardwalk!

9.8 out of 10, Exceptional, (39)
"The stay was all we hoped for. Walkable to the boardwalk, beach with passes, coffee shop and restaurants. Front curb parking. And the outdoor sitting space was like being at home. Plenty of space, grill and fenced with beautiful plants. We didn't mind the smaller space as it has everything including a stocked kitchen. Really cute comfortably decorated. And full communication with Tammy. "
Blocks to the Boardwalk!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (42)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
The Lazy Crab Beach House - Free beach passes
Welcome to The Lazy Cat North Beach, featuring a charming front porch with a potted plant and a decorative welcome sign.

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"Great stay"
The Lazy Crab Beach House - Free beach passes
Screened Patio, Deck & Grill: Saint Inigoes Home!
Enjoy al fresco dining with a view of the surrounding landscape from this outdoor space featuring a table and chairs.

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.8 out of 10, Exceptional, (6)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!
Million Dollar View of the Chesapeake Bay
Enjoy a serene sea view from this corner room, featuring a round table and comfortable seating for four.

Million Dollar View of the Chesapeake Bay

9.8 out of 10, Exceptional, (124)
"Very clean, everything you need plus! Close to DC, Annapolis, Arlington National Cemetery and many more we didn’t have time for! Ordering dinner out and bringing it back to the house to eat while watching a movie and just enjoy watching the view! The view of the Bay is breathtaking!!!!!!Highly recommend the MACC Church if your looking for a church.We drove 16 hours one way to get there and we would do it again!Blessings"
Million Dollar View of the Chesapeake Bay
Pet-Friendly Maryland Home on the Potomac River!
Enjoy a peaceful meal by the water with a hammock nearby for relaxation.

Pet-Friendly Maryland Home on the Potomac River!

10.0 out of 10, Exceptional, (2)
"Property was well maintained, very comfortable, and easy to access. Anything you might want was a short drive away but you feel like you are in a remote paradise. "
Pet-Friendly Maryland Home on the Potomac River!
4BDRM River front house with Private Beach in Hollywood
Relax in Adirondack chairs on the dock, overlooking the serene water and surrounding trees.

4BDRM River front house with Private Beach in Hollywood

2.0 star property
9.8 out of 10, Exceptional, (8)
"This house was just what we needed for our business associates. "
4BDRM River front house with Private Beach in Hollywood
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Cozy seating area with a fireplace, sofas, and a coffee table.

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

10.0 out of 10, Exceptional, (7)
"Nice location. The house had everything we needed for our stay. The host was available by phone for any questions we had. I would stay again the next time I visit North Beach"
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
Your private beach retreat in historic St. Mary's
Enjoy cooking in this well-equipped kitchen with a central island, refrigerator, oven, and dishwasher.

Your private beach retreat in historic St. Mary's

10.0 out of 10, Exceptional, (25)
"This was the perfect house for our family trip to St. Mary's -- nicely upgraded, well stocked and beautiful views. Will definitely return."
Your private beach retreat in historic St. Mary's
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Relax in comfort under a striped umbrella, surrounded by the soothing sounds of the sea.

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

10.0 out of 10, Exceptional, (72)
"We had a great time. Private beach, spacious house, kayaks!"
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Coastal Haven- Beach w/ BBQ
Surrounded by a serene beach and calm waters, this tranquil setting features a majestic tree trunk.

Coastal Haven- Beach w/ BBQ

10.0 out of 10, Exceptional, (15)
"This house is amazing on a nice quiet street. We enjoyed our stay as it felt like we were home. Clean and cozy a lot of extra room we will be back next year for sure."
Coastal Haven- Beach w/ BBQ
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
"Staff was amazing "
janel 2-night trip
Posted 1 day ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG