Southern Maryland vacation rentals

We found 1,371 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024

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Take in the waterfront beauty of Southern Maryland

Enjoy the live music and other features of Southern Maryland. This city's sporting events, boating and shopping draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Southern Maryland

Are you looking for top things to see and do during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Southern Maryland a fun place to get away. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Maryland International Raceway (9.4 mi / 15.1 km)
  • Chesapeake Beach Water Park (16.4 mi / 26.3 km)
  • Caledon State Park (25.6 mi / 41.2 km)
  • Six Flags America (27.6 mi / 44.4 km)
  • Running Hare Vineyard (5.9 mi / 9.5 km)
  • White Plains Golf Course (11.3 mi / 18.2 km)

Exploring the natural features in Southern Maryland

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Southern Maryland is a great place to get out in nature. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • Breezy Point Beach (14 mi / 22.5 km)
  • Calvert Cliffs State Park (17.8 mi / 28.7 km)
  • St. Mary's River State Park (19.9 mi / 32 km)
  • Colonial Beach (21.9 mi / 35.3 km)
  • Potomac River Waterfront Park (25.1 mi / 40.4 km)
  • Caledon State Park (25.6 mi / 41.2 km)

Frequently asked questions

What is the best area to stay in Southern Maryland when booking a vacation rental?

One of the most sought-after destinations to choose your Vrbo vacation rental in Southern Maryland is Fort Washington. Base yourself here and explore its must-see attractions, including Fort Washington Park and Fort Washington Marina.

What is the most popular type of vacation rental accommodation in Southern Maryland?

Based on our data, houses are the most in-demand vacation rental type in Southern Maryland. But that goes without saying, everyone's idea of the perfect trip isn't going to be the same. Vrbo has vacation rentals of all shapes, sizes and budgets, so you're bound to find the perfect match.

How much does it cost to rent a vacation rental in Southern Maryland?

Season, property type and length of stay are some things that can affect the price of a vacation home. Simply click on your travel dates to find your ideal match. From homey country cottages to expansive villas, all Vrbo vacation rentals offer incredible value.

How much does it cost to rent a beach house in Southern Maryland?

When you travel and the style and size of the property will help determine the cost of your beachside stay. Put in your Southern Maryland travel dates to see your options on Vrbo. Did someone just say "private pool"? Use our filters to select the amenities and features you want in your beach house.

What are popular rental amenities in Southern Maryland?

A fridge, a microwave oven and off-street parking options head the list of most popular rental amenities in Southern Maryland. Whether you plan to go on your own, with your significant other or as a family, Vrbo can help you find a vacation home that suits your tastes with all the features you'll enjoy.

Are there large group vacation rentals in Southern Maryland?

Southern Maryland has 33 vacation rentals that can cater to 10 or more guests. These properties come with the space you need to enjoy good times with loved ones.

What are the top attractions for families in Southern Maryland?

Keep the kids busy at these top family-friendly attractions in Southern Maryland:

  • Calvert Cliffs State Park
  • St. Charles Towne Center
  • Chesapeake Beach Water Park

Can I find two-bedroom vacation rentals in Southern Maryland?

Choose from 45 two-bedroom properties in Southern Maryland. Give the kids the second room or fill it with a couple of your favorite people. There's plenty of space for whoever's lucky enough to be coming along for the ride.

Are there vacation rentals with WiFi in Southern Maryland?

You can pick from 112 vacation rentals with WiFi in Southern Maryland. If you'd like to disconnect from the world during your trip, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How old do you have to be to rent a vacation rental in Southern Maryland?

The minimum age permitted can vary across properties on Vrbo, so look at the rules of the vacation home in Southern Maryland you're interested in. But typically, it's 16, 18 or 21.

How long can I rent a vacation rental in Southern Maryland for?

It really depends on the Southern Maryland property. To look at a list of options offering extended stays, simply enter your dates and number of guests into the Vrbo search page. You can enjoy having the property to yourself, as well as comforts such as a full kitchen, air conditioning and a backyard where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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