A rural landscape with a barn, trees, and a fence under a sunset sky.

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Check availability on Leonardtown 5 Star Hotels

Tonight
Sep 16 - Sep 17
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Sep 17 - Sep 18
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Sep 18 - Sep 20
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Sep 25 - Sep 27

Our top choices for Leonardtown 5-star hotels

Reception
Fireplace
Executive lounge
Exterior

1. Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland
Ridge
United States
Heinz J.
$335 nightly
$372 total
Sep 24 - Sep 25
Total with taxes and fees
Swanendele Inn at St. Mary's Maryland
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Learn more about Leonardtown

Explore the historic waterfront square where local artisans showcase their crafts and restaurants serve fresh Chesapeake Bay seafood. Kayak along Breton Bay's peaceful waters or visit the nearby Patuxent River Naval Air Museum in Lexington Park.

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A lakeside view with trees, a wooden dock, and a small shed.

Top Leonardtown Hotel Reviews

Find out more about Leonardtown

Ready for an incredible adventure? Add even more luxury on your next trip to Leonardtown by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Leonardtown so popular in the last year. There's no reason to delay a getaway to Leonardtown any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Leonardtown and get ready to be pampered like never before. Don't wait any longer!

Book the Best Leonardtown 5-Star Hotels

You'll have a fantastic time at one of these 5-star hotels. Exceptional customer care, granite-tiled bathrooms, and fabulous spa offerings are waiting for you. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. What kind of amenities will make your stay a wonderful one? A body scrub that will leave you feeling great? 24-hour room service, so you can order that filet mignon in the wee hours of the morning? A rejuvenating facial treatment to help your cares fall away?

Can't wait to get outside? Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Leonardtown are the perfect place to relax after a busy day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Make Your Escape

The results are in, and Leonardtown 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Opt for one of the 5-star hotels in Leonardtown today and dive into in the lap of luxury at your convenience.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Leonardtown?
The amount you pay for a 5-star hotel in Leonardtown can vary according to when you prefer to travel and how long you plan to stay, among a range of factors. Take advantage of our price per night filter and other search tools to find the best rate on a luxurious getaway.
  • Search for the lowest price per night from $372
What makes a hotel 5 stars in Leonardtown?
Impeccable guest service is the hallmark of every 5-star hotel in Leonardtown. From the moment you enter the lobby, staff cater to your every need, whether arranging valet parking or providing a nightly turn-down service. Also, hotels must offer superior conveniences to be considered for a 5-star rating. These can include luxury bathrooms, a wellness center, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Leonardtown?
Use our handy filters to find a luxurious retreat in Leonardtown where everything you need is included in the price. After your initial search, refine your results for properties that have 5 stars and are deemed "All inclusive." The first thing on the schedule at these stays? Pure enjoyment and indulgence.

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