246+ Private Villas and Holiday Rentals in Leonardtown |
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Leonardtown Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Leonardtown

Discover more than 246 vacation rentals available in Leonardtown. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Leonardtown.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Leonardtown, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Leonardtown. On average, places to stay near Leonardtown offer 971.94 ft², with nightly prices averaging GB £258.

With Casai, finding and comparing holiday rentals in Leonardtown is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Leonardtown

Type Count
Vacation Homes 157
Cottages 28
Holiday Apartments 16
Villas 1

Use these Quick Filters to Find a Holiday Rental in Leonardtown

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Leonardtown.

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

Top Attractions Around Leonardtown, MD

Casai offers a large selection of top attractions around Leonardtown . Research things to do on your vacation before you visit Leonardtown.


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

Other Places to Stay in Leonardtown, MD


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

Frequently Asked Questions About Leonardtown?

What are the top holiday rentals in Leonardtown?

With numerous options available in Leonardtown, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Leonardtown:

How many holiday rentals have private pools in Leonardtown?

Discover a selection of holiday rentals with private pools near Leonardtown with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Leonardtown are best for families?

If you're searching for a family-friendly holiday home in Leonardtown, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Leonardtown:

How many Casai.uk holiday rentals are available in Leonardtown?

As of 2025, Casai boasts over 246 properties listed in the Leonardtown area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Leonardtown.


People Also Ask

There are 246 Leonardtown, MD Holiday Rentals

Recently Booked Holiday Rentals in Leonardtown