House vacation rentals in Southern Maryland

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Top-rated house rentals in Southern Maryland

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.

Home in Mechanicsville

5.0 out of 5 average rating, 105 reviews

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

ValueFamilyQuiet

Top guest favorite

A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.

Home in Leonardtown

4.94 out of 5 average rating, 100 reviews

The River House: A private waterfront oasis…

Cozy up by a roaring fire with your partner and relish the winter chill! This private waterfront retreat offers panoramic water views of the Potomac River and sits at the mouth of Breton Bay. At the end of the road and occupying two acres, the property is a private oasis of year-round natural beauty. You’ll have 650’ of waterfront to yourself to lounge at the waterside tiki-bar deck, on the screened-in porch, on the house deck, in the yard or on the hammock. Kayak, canoe, chill however you like!

LocationFamilyRiver

Top guest favorite

A wooden dock extends into calm waters, showcasing a boat moored at the end. The serene surface reflects the pastel colors of the sky during dusk. Wooden posts line the edges of the dock, enhancing the tranquil setting.

Home in Newburg

4.91 out of 5 average rating, 128 reviews

The River House, a Wicomico Beach Retreat

Located right on the water of the Wicomico River with a private sandy beach, The River House will become your favorite retreat! This 5 bdrm, 3 bath fully stocked home has all the convenience of modern construction (including wifi) but maintains the vintage charm of the original property. The acre+ plot is very private with spectacular forest & water views. Fun can be found in every direction and for all ages! It has two bottom floor bed/bath combos, plus a fabulous sleeping loft for the kids!

ValueFamilyBeach

Top guest favorite

An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.

Home in Cobb Island

4.99 out of 5 average rating, 140 reviews

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

FamilyValueComfort

Top guest favorite

A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.

Home in Lusby

4.95 out of 5 average rating, 144 reviews

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

FamilyValueSleep quality

Top guest favorite

The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.

Home in Solomons

5.0 out of 5 average rating, 139 reviews

The Little House on Back Creek

Get away and relax at this peaceful, very private and centrally-located home in the heart of Solomons Island on Back Creek with beautiful water views overlooking Solomons Harbour. The property is shared with Jacqueline Morgan Day Spa and The Blue Shell Gifts and Décor. Just a quick walk to a enjoy a massage, facial, mani/pedi, salon services and shopping! Enjoy fishing, kayaking, bicycling, walk to so many great restaurants nearby and bring your boat! Docking is available during your stay.

LocationFamilyHospitality

Top guest favorite

Home in Cobb Island

4.97 out of 5 average rating, 102 reviews

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

LocationFamilyCondition

Top guest favorite

Home in Montross

4.98 out of 5 average rating, 158 reviews

Waterfront, 3 Beaches, Dock+Kayaks, Potomac, 7 ppl

Relax - Star Gaze - Kayak/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨‍🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in the Northern Neck of VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!

LocationFamilyParks

Top guest favorite

A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.

Home in Montross

4.97 out of 5 average rating, 108 reviews

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

LocationFamilyHot tub

Top guest favorite

An exterior view of the home showcases a light grey facade with a gentle slope roof surrounded by trees. A gravel driveway leads to the entrance, while a calm waterway with a boat dock is visible in the background.

Home in Hollywood

4.99 out of 5 average rating, 106 reviews

Waterfront Home: Osprey Getaway

Welcome to The Osprey Getaway! This spacious home is the perfect destination for families seeking a relaxing retreat. Our home is not far from Solomon’s Island, Patuxent River Naval Air Station, St. Mary’s College of Maryland, and historic Leonardtown. Here you'll find an open floor plan and plenty of space to unwind and take in your surroundings. Enjoy the peace and quiet of Cuckold Creek and the beauty of our newly renovated home. We can't wait to share our home with you!

FamilyLocationSleep quality

Top guest favorite

A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.

Home in Dameron

4.99 out of 5 average rating, 142 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

LocationValueIndoor spaces

Guest favorite

A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.

Home in Montross

4.86 out of 5 average rating, 103 reviews

Potomac River Getaway

Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!

FamilyValueSleep quality