Southern Maryland Holiday Rentals from €231: Search Short-Term Rentals

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Holiday Rentals in Southern Maryland

Relax on the lakeside deck with two comfortable lounge chairs and a shaded area.

"We stayed here for the weekend while attending a car show at the raceway close by. Very private and welcoming. Great place to relax and unwind after a long day. "

Relax on the deck with ocean views, featuring a table and chairs.

"The views are fantastic. Very quiet neighborhood. "

"The place was inviting and beautiful. Will definitely stay there again."

Enjoy cooking in this well-equipped kitchen with a double oven, large refrigerator, and shelf.

"It was a great stay!"

Relax on the spacious deck with a wicker sofa, cushioned chairs, and a hammock, perfect for unwinding in a serene atmosphere.

"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."

Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

Enjoy a marina view from the bay window, featuring a glass-top table and chair.

"The location is great with amazing views of the docks and very walkable to the boardwalk, restaurants, and the Solomon museum. Apartment was cozy with great communication from the hosts. Would recommend to anyone! "

includes taxes & fees

11 Aug - 12 Aug

Enjoy a serene lakeside escape with a picnic table and access to a pebbly beach.

"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "

includes taxes & fees

29 Jul - 30 Jul

Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."

Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"

Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

"Awesome home wnd location! Would stay again!"

Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

"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.). "

Charming single-story house with a front porch and well-manicured lawn.

"Lovely, serene, comfortable, waterfront home. Conveniently close to the essentials, restaurants, pier, beach, markets, and more. "

Relax in a stylish space with a plush sofa, dining area, and large window.

"Great stay, clean & owner gave great local suggestions!"

Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Enjoy the ocean view from the deck, featuring a comfortable seating area with a table and chairs.

"Stayed with two other families for the State Swim Championships. Property is spacious, clean and well appointed. Even the kitchen knives were sharp!"

Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large island, and a sink.

"Awesome house a very short walk from Herrington Harbour."

Walk along the beach to the wooden pier, where the calm waters await.

"The accommodations were superb and being on the water was amazing!"

includes taxes & fees

29 Jul - 30 Jul

Enjoy cooking and dining in this well-equipped kitchen with appliances and a central island.

"The host were helpful and easy to work with. Property was thoughtfully outfitted with everything we needed. Great location."

"Such a great accommodation!!! We were here for a swim meet in town and Katie was the greatest host. We had all the comforts and amenities needed. We will def be staying again. "

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Top Southern Maryland Hotel Reviews

Executive Inn And Suites

10/10 Excellent

"Very nice conveniently located property "

Wingate by Wyndham Waldorf/Washington DC Area

10/10 Excellent

"Overall, we had an excellent stay! The hotel was beautiful, the staff was friendly, and the amenities were top-notch. The only downside—and the reason for the half-star deduction—was that our room wasn’t cleaned by 3:00 PM, which seemed to be treated as normal without any explanation or apology. Aside from that minor inconvenience, everything else exceeded expectations. Would definitely stay again!"

Find out more about Southern Maryland

Everything you need to know about Southern Maryland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southern Maryland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southern Maryland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southern Maryland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southern Maryland. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southern Maryland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southern Maryland holiday rentals we have selected for you start as low as €231 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southern Maryland rentals

At Expedia, we put the best Southern Maryland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southern Maryland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southern Maryland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southern Maryland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Holiday Rentals in Southern Maryland

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Holiday Rentals in Southern Maryland

Waterfront cottage for paddle boarding, kayaking, crabbing, and fishing

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

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

A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach

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

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

Waterfront Solomons Apartment

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

The Blue Crab Beach House - Free beach passes

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

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

Waterfront Wildlife Retreat on the Patuxent River

Bayfront Maryland Retreat w/ Deck, Near Beaches!

Terrace Suite · Terrace Suite - Private Flat in Historic Manor.

Rising Sun Bay View Cottage

Hays Beach House - Hot Tub - Private Beach

Updated North Beach Cottage: Pet Friendly!

Cottage Located on the Patuxent River!

Bay views with kayaks, bikes, fire pit, crabbing and more

Tiny, Funky, and Full of Love - Welcome to the Love Shack

Top Southern Maryland Hotel Reviews

Executive Inn And Suites

Holiday Inn Express Waldorf by IHG

Wingate by Wyndham Waldorf/Washington DC Area

Country Inn & Suites by Radisson, Camp Springs (Andrews Air Force Base), MD

Rod 'N' Reel Resort

Sleep Inn & Suites Near Joint Base Andrews - Washington Area

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Hampton Inn & Suites National Harbor - Alexandria Area

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Find out more about Southern Maryland

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