Southern Maryland Holiday Rentals from €263: Search Short-Term Rentals

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Holiday Rentals in Southern Maryland

"Awesome home wnd location! Would stay again!"

"The views are fantastic. Very quiet neighborhood. "

"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"

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

"The place had everything we needed and the yard was great for the dogs. Would definitely stay here again."

"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. "

"We really enjoyed our stay on Solomon’s Island. The apartment was the perfect location to enjoy the island’s amenities. The bed was really comfortable and shower great. The view from the living room was spectacular. "

includes taxes & fees

5 Sept - 6 Sept

"Modern, Fresh, Clean! No complaints at all!"

"We enjoyed the property lots of wildlife around enjoyed kayaking and crabing . "

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

includes taxes & fees

24 Aug - 25 Aug

"My daughter and I enjoyed the place, especially the pool. She really loved the bunk-beds too. I asked for an early check in and that was granted which gave my daughter and I more time to explore the area and Calvert Cliffs. It did rain the entire time which dampened the exploring, and it was low 70s in August for swimming, but we made the most of it and had enjoyable memories."

On the beach, sun-loungers, beach towels

"If you want to relax by the water and getaway from the hustle and bustle, this is the place. The cottage is updated and cozy with amazing views. Just step off the patio onto the sand. Cottage was stocked with essentials and extra goodies to make it feel like home."

"A very nice house with an amazing view 10/10 recommend"

"Rented the house to celebrate a graduation from St Mary’s College. It was perfect. "

Iron/ironing board, free WiFi, bed sheets

"Very nice room with good accessibility for someone with limited mobility. The room description in Expedia was completely accurate, and we loved the accessibility features. The location is very close to good restaurants that also have good accessibility."

"Great for our group of 2 families. Plenty of beds, nice gathering space, access to the creek, played in the grassy field. Would/will likely return! "

"The property was very comfortable, convenient, well organized and beautifully prepared. "

"This property was everything we wanted. We hope to return next year."

Beach nearby, sun-loungers, beach towels

"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."

"we stayed for work, plenty of things to do in the area. plenty of space in the house. everything was clean."

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Top Southern Maryland Hotel Reviews

Rod 'N' Reel Resort

10/10 Excellent

"This was my first time staying at this resort and it was very nice. Great staff, very clean, and good food in the restaurants. "

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 €263 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

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

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

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

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

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

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

Waterfront Solomons Apartment

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

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

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

Maryland Vacation Rental w/ Private Pool & Dock

Private Beach Front Getaway at The Sunshine Beach Cottage.

New! Cozy River Cottage with great views of the water!

Waterfront Wildlife Retreat on the Patuxent River

Guest Quarters at the Inn - 103

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

Walk to Beach: Elegant Escape in Lusby!

Bright and airy waterfront getaway

The Blue Crab Beach House - Free beach passes

2 Mi to Lighthouse: Waterfront Home w/ Dock!