Title: 5 Stars Hotels in Leonardtown, Maryland from CA $428 - Find Cheap Leonardtown Hotels With 5 Stars | Expedia.ca [Leonardtown Travel Guide](https://expedia.ca/Leonardtown.dx6063192)[Hotels in Leonardtown](https://expedia.ca/Leonardtown-Hotels.d6063192.Travel-Guide-Hotels)[Vacation Rentals in Leonardtown](https://expedia.ca/Leonardtown-Vacation-Rentals.d6063192.Travel-Guide-VacationRentals)[Flights to Leonardtown](https://expedia.ca/Cheap-Flights-To-Leonardtown.d6063192.Travel-Guide-Flights)[Leonardtown Car Rentals](https://expedia.ca/Car-Rentals-In-Leonardtown.d6063192.Car-Rental-Guide)[Leonardtown Vacation Packages](https://expedia.ca/Leonardtown.d6063192.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/cf4f52b435dd2053050c5c0216fb1fcb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Pla Jira # 5 Stars Hotels in Leonardtown, Maryland from CA $428 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Leonardtown 5 Star Hotels Tonight [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=6063192&startDate=2025-10-16&endDate=2025-10-17&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 17 - Oct 18](https://www.expedia.ca/Hotel-Search?regionId=6063192&startDate=2025-10-17&endDate=2025-10-18&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6063192&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6063192&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Leonardtown 5 Star Hotels ![Reception](https://images.trvl-media.com/lodging/96000000/95420000/95417700/95417680/232b5209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/96000000/95420000/95417700/95417680/612569f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/96000000/95420000/95417700/95417680/58f012a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/96000000/95420000/95417700/95417680/5766841b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Swanendele Inn at St. Mary's Maryland Ridge 9.8/10 Exceptional (32) "Beautiful inn with attentive and welcoming staff." CA $386 CA $428 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Ridge-Hotels-Swanendele-Inn-At-St-Marys-Maryland.h95417680.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Leonardtown-Hotels.s50-0-d6063192.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Leonardtown-Hotels.s50-0-d6063192.Travel-Guide-Filter-Hotels) ## 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](https://www.expedia.ca/Hotel-Search?startDate=2025-10-30&endDate=2025-10-31&adults=2®ionId=6063192) ![](https://mediaim.expedia.com/destination/2/cf4f52b435dd2053050c5c0216fb1fcb.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Pla Jira ## Top Leonardtown Hotel Reviews ## Find out more about Leonardtown ## Five Star Hotels in Leonardtown There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Leonardtown so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Leonardtown and get ready to be pampered like never before. #### Get a Great Deal on 5-Star Hotels in Leonardtown Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places. Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town. #### Make Your Escape to Leonardtown The results are in, and Leonardtown 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Leonardtown! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Leonardtown today and settle down in the lap of luxury tomorrow. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Leonardtown? > You can find several pricing options for 5-star hotels in Leonardtown on Expedia. How much you'll pay will depend on when you want to travel, length of your trip and other factors. Compare all of the available properties for your preferred dates and make use of our pricing and other filters to discover the ideal luxury stay. > > > > - Search for the lowest price per night from CA $428 ### What makes a hotel 5 stars in Leonardtown? > Impeccable guest service is the foundation of every 5-star hotel in Leonardtown. From the moment you arrive, staff are at your beck and call, whether offering luggage assistance and storage or providing in-room massage treatments. On top of that, hotels must feature upscale conveniences to obtain a 5-star rating. These can include luxury bathrobes, spa facilities, swimming pools, gastronomic restaurants and knowledgeable concierge. ### Are there any 5-star all-inclusive resorts in Leonardtown? > Find an indulgent getaway that includes your lodging, meals, drinks and entertainment in Leonardtown with Expedia's filters. Search for resorts rated 5 stars and click on the "All inclusive" filter. Be sure to check what's included in the price. 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