Southern Maryland holiday rentals

We found 1,552 holiday rentals — enter your dates for availability

Find spaces that suit your style

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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Southern Maryland

Are you looking for attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Southern Maryland a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Running Hare Vineyard (5.9 mi / 9.5 km)
  • Maryland International Raceway (9.4 mi / 15.1 km)
  • Chesapeake Beach Water Park (16.4 mi / 26.3 km)
  • Lake Presidential Golf Club (23.1 mi / 37.3 km)
  • Caledon State Park (25.6 mi / 41.2 km)
  • Greendale Golf Course (27.5 mi / 44.2 km)

Exploring the natural features in Southern Maryland

Whether you're looking for adventure or just want to appreciate the scenery, Southern Maryland is a great place to spend some time outside. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Breezy Point Beach (14 mi / 22.5 km)
  • Annmarie Sculpture Garden and Arts Center (18.9 mi / 30.5 km)
  • St. Mary's River State Park (19.9 mi / 32 km)
  • Piscataway Park (20.8 mi / 33.5 km)
  • Colonial Beach (21.9 mi / 35.3 km)
  • Mount Vernon Trail (22.5 mi / 36.2 km)

Frequently asked questions

What is the best area to stay in Southern Maryland when booking a holiday home?
One of the most sought-after destinations to choose your Stayz holiday home 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 holiday home accommodation in Southern Maryland?
Based on our data, houses are the most in-demand holiday home type in Southern Maryland. But that goes without saying, everyone’s idea of the perfect trip isn’t going to be the same. Stayz has holiday homes of all shapes, sizes and budgets, so you’re bound to find the perfect match.
How much does it cost to rent a holiday home in Southern Maryland?
Season, property type and length of stay are some things that can affect the price of a holiday home. Simply click on your travel dates to find your ideal match. From homey country cottages to expansive villas, all Stayz holiday homes 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 Stayz. Did someone just say “private pool”? Use our filters to select the amenities and features you want in your beach house.
What are popular home amenities in Southern Maryland?
A fridge, a microwave oven and off-street parking options head the list of most popular home amenities in Southern Maryland. Whether you plan to go on your own, with your significant other or as a family, Stayz can help you find a holiday home that suits your tastes with all the features you’ll enjoy.
Are there large group holiday homes in Southern Maryland?
Southern Maryland has 33 holiday homes 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 Centre
  • Chesapeake Beach Water Park

Can I find two-bedroom holiday homes 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 favourite people. There’s plenty of space for whoever’s lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Southern Maryland?
You can pick from 112 holiday homes 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 Stayz.
How old do you have to be to rent a holiday home in Southern Maryland?
The minimum age permitted can vary across properties on Stayz, so look at the rules of the holiday home in Southern Maryland you’re interested in. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home 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 Stayz 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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