Leonardtown Vacation Rentals
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Our top choices for Leonardtown vacation rentals

Anne & Fred`s Leonardtown Home W/ Arcade room!
Anne & Fred`s Leonardtown Home W/ Arcade room!
Cheery, Peaceful Water Front Cabin on Winery Grounds
Cheery, Peaceful Water Front Cabin on Winery Grounds
Soul Oasis - home on the Chesapeake Bay
Soul Oasis - home on the Chesapeake Bay
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Cottage Located on the Patuxent River!
Cottage Located on the Patuxent River!
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Cozy centrally located studio with WiFi and AC in peaceful Port Republic, MD
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.Find vacation rentals that suit your style
Top Leonardtown Hotel Reviews

Hampton Inn Dahlgren
Find out more about Leonardtown
Everything you need to know about Leonardtown vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leonardtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leonardtown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Leonardtown vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Leonardtown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Leonardtown in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $205 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Leonardtown rentals
At Expedia, we put the best Leonardtown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Leonardtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leonardtown vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leonardtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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