Southern Maryland Holidays

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Our guide on where to stay in Southern Maryland

Find the best Southern Maryland areas and neighborhoods for the activities you enjoy most. Learn more about Southern Maryland
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Point Lookout

If you're spending some time in Point Lookout, Point Lookout State Park and Chesapeake Bay are top sights worth seeing.

Find hotels in Point Lookout

Southern Maryland Holiday

Our pick of the best Southern Maryland Hotel Deals

Gaylord National Resort & Convention Center

Gaylord National Resort & Convention Center

4 out of 5
201 Waterfront Street Fort Washington MD
Fully refundableReserve now, pay when you stay
The price is NZ$511 per night from 22 May to 23 May
NZ$511
22 May - 23 May
includes taxes & fees
8.8/10 Excellent! (1,025 reviews)
Beautiful property and enjoyed my stay!

Reviewed on 3 May 2026

Gaylord National Resort & Convention Center
Spark by Hilton Waldorf

Spark by Hilton Waldorf

3 out of 5
11770 Business Park Drive Waldorf MD
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 17 May to 18 May
NZ$168
17 May - 18 May
includes taxes & fees
8.2/10 Very Good! (127 reviews)
Breakfast was good but just to early on the weekend.

Reviewed on 30 Apr 2026

Spark by Hilton Waldorf
Red Roof PLUS+ Washington DC - Oxon Hill 

Red Roof PLUS+ Washington DC - Oxon Hill 

2.5 out of 5
6170 Oxon Hill Road Oxon Hill MD
Fully refundableReserve now, pay when you stay
The price is NZ$177 per night from 7 May to 8 May
NZ$177
7 May - 8 May
includes taxes & fees
7.2/10 Good! (1,009 reviews)
Do not book. See reviews

Reviewed on 2 May 2026

Red Roof PLUS+ Washington DC - Oxon Hill 
See all 751 properties in Southern Maryland
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.

Discover the most popular places to visit in Southern Maryland

George Washington's Mount Vernon

George Washington's Mount Vernon

Gain fascinating insights into the life of America’s first president at this beautifully restored country estate set on the shores of the Potomac River.

George Washington's Mount Vernon
The Beach at Calvert Cliffs. Maryland, USA, Maryland

Calvert Cliffs State Park

You can take time to visit Calvert Cliffs State Park during your travels to Lusby. Amble around this family-friendly area's riverfront or attend a sporting event.

Calvert Cliffs State Park
Chesapeake Beach Water Park

Chesapeake Beach Water Park

Have a fun-filled day with the family at Chesapeake Beach Water Park as part of your trip to Chesapeake Beach. Visit the spas in this relaxing area or simply enjoy its restaurants.

Chesapeake Beach Water Park

Frequently asked questions

Can I cancel my flight booking to Southern Maryland due to COVID-19?
Our handy Customer Service Portal has useful information about cancelling your Southern Maryland flight due to COVID-19. Before you reserve a seat, it's a good idea to read the terms and conditions of your chosen airline too.
What's the best way to find cheap flights to Southern Maryland that have flexible change policies?
Search for your affordable airfares to Southern Maryland, then mark the "No change fee" box directly underneath the "Flexible change policies" subheading. It's as easy as that. We appreciate that travel plans can change and flexibility matters, so you can book with confidence with Expedia.
What are some of the general tips for travellers to Southern Maryland during the COVID-19 outbreak?
If it's your first time travelling during the COVID-19 pandemic, you'll notice a raft of new restrictions and rules in place. Follow these tips and make your trip to Southern Maryland go off without a hitch:
  • Before booking your flight, see if any travel restrictions apply — in both your destination and origin. Get the latest updates by reviewing government websites.
  • Requirements state that you must wear a face mask at the airport, even at screening checkpoints. Be prepared to lower your mask for identification purposes when asked by a TSA officer.
  • To reduce the possibility of cross-contamination, position your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA employee.
  • TSA is now permitting passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on baggage. This will need to be removed from your bag to be screened.
  • Remove personal items from your pockets, such as your wallet, phone and small change, and place them in your carry-on instead of the bins. This will reduce handling during the screening process.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Separating food from your carry-on means it's less likely a TSA agent will need to open and touch your bag for inspection.

Which airlines fly to Southern Maryland?
American Airlines is a top carrier servicing Southern Maryland. Search for a fare to Ronald Reagan Washington National Airport (DCA) and you'll have 5326 American Airlines flights every month to pick from.
How can I find cheap tickets to Southern Maryland?
To get your hands on a great deal to Southern Maryland, book ahead of time. Also use Expedia's handy "flexible dates" feature above your search results. This will compare the cheapest prices for similar time frames. In the last seven days, was the best price for a flight to Southern Maryland.
How much is a flight to Southern Maryland?
You could have picked up a return airfare to Southern Maryland from anywhere between and in the last seven days. For one-way journeys departing from (), the lowest amount paid during this time was .
What are the most popular airports to fly into in Southern Maryland?
Jet into Ronald Reagan Washington National Airport (DCA) and sample all that Southern Maryland has to offer. As the region's main entry point, about 7771 flights land here every month.
When is the cheapest time to fly to Southern Maryland?
Consider travelling early on in the week to land a bargain airfare to Southern Maryland. Tuesday is usually the most affordable day to fly, with Monday a close second. Saturday typically has the most expensive ticket prices. This is because many people like to begin their trip on a weekend.
How much is a plane ticket to Southern Maryland?
In the last seven days, airfares to Southern Maryland varied between and . Prices depend on the departure time, airline, seating class and when you make your booking.
Which airlines with flights to Southern Maryland employ COVID-19 cleanliness policies?
In an effort to reduce contact between passengers and flight crew during the current pandemic, most airlines have taken physical distancing and other measures to the skies. Just some of these are:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.