Compare and book 5 Star hotels in Leonardtown, Maryland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Leonardtown 5 Star Hotels

Tonight
2 Dec - 3 Dec
Tomorrow
3 Dec - 4 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Leonardtown 5 Star Hotels

Reception
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, (32)
"Beautiful inn with attentive and welcoming staff."
United States
Chris
Swanendele Inn at St. Mary's Maryland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.

See all hotels in Leonardtown
Breton Bay panorama

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

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.

Explore a world of travel with Expedia