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

Compare and book 5 Star hotels in Leonardtown, Maryland

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Check availability on Leonardtown 5 Star Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Leonardtown 5-star hotels

Reception

1. Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland
5.0 star property
Ridge
9.8 out of 10, Exceptional, (34 reviews)
"A beautiful stay with amazing hosts!"
United States
Vineet
The price is 8.407.667 ₫
9.332.510 ₫ total
includes taxes & fees
6 Aug - 7 Aug
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

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 depends on things such as when you plan to go and the length of your getaway. A top tip for bagging the best deal? Use our pricing filters to compare all of the available accommodation for your selected dates.

  • Search for the lowest price per night from 9.332.510 ₫

What makes a hotel 5 stars in Leonardtown?
In Leonardtown, a hotel needs to offer a specific number of upscale amenities to be designated 5 stars. These can include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their guest-centric standard of service. You can look forward to things like in-room massages, concierge services and nightly turn-down services. Some may even offer extra touches such as a welcome gift.
Are there any 5-star all-inclusive resorts in Leonardtown?
Use our filters to find a luxurious getaway in Leonardtown where most of what you need is included. After your initial search, narrow down your results for properties that have a rating of 5 stars and are listed as "All inclusive." The first thing on the to-do list at these stays? Relaxation and enjoyment.