245+ Rental Villas and Private Getaways in Leonardtown |
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Leonardtown Villa Rentals

About Leonardtown Vacation Rentals

There are more than 245 incredible getaway rentals that are available in Leonardtown. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Leonardtown.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Leonardtown, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Leonardtown. Places to stay near Leonardtown are 970.61 ft² on average, with prices averaging CA $487 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Leonardtown. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

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Top Private Villas, Resorts, and Rentals in Leonardtown

Type Count
Vacation Homes 157
Cottages 28
Holiday Apartments 15
B&B 4
Cabin Rentals 3
Others 2
Unique Vacation Rentals 1
Ski Chalet Rentals 1
Villas 1

Use these Quick Filters to Find a Vacation Rental in Leonardtown

★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Leonardtown with BedroomVillas.

Weather in Leonardtown, MD

View the weather forecast for Leonardtown before booking your Leonardtown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near Leonardtown's Top Attractions

A Large Selection of Villas and Vacation Rentals from Around the World Leonardtown's Research Top Attractions For Your Vacation


Port of Leonardtown Winery
Patuxent River Naval Air Station
Maryland International Raceway
St. Mary's College of Maryland
Calvert Cliffs State Park
Point Lookout State Park
Westmoreland State Park
St. Mary's River State Park
Historic St. Mary's City
Budds Motorcross Speedway
Bayside Marina
Cove Point Lighthouse
Hague Winery
Running Hare Vineyard
Stratford Hall Plantation
Aqualand Marina
Warsaw Town Park
Cecil's Old Mill
Ingleside Vineyards

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Port of Leonardtown Winery 219 Properties
St. Mary's County 142 Properties
Compton 25 Properties

Frequently Asked Questions About Leonardtown?

What are the top hotels or resorts in Leonardtown?

We provide an array of great vacation destinations in Leonardtown. If you are looking to stay in or around the Leonardtown area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Leonardtown:

How many vacation rentals have private pools in Leonardtown?

We have 5 luxury villas and vacation rentals featuriung a private pool in and near Leonardtown. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Leonardtown is best for families?

Searching for a family-friendly getaway in Leonardtown? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Leonardtown?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 245 in the Leonardtown area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Leonardtown. 


People Also Ask

There are 32 hotels in Leonardtown and 176 rentals

Recently Booked Hotels, Resorts, or Rentals in Leonardtown