Find 5 Star Hotels in Leonardtown, MD

  • 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

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 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

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.

Explore a world of travel with Expedia