Title: Leonardtown Vacation Packages 2026 from $370 | Expedia.com [Leonardtown Travel Guide](https://expedia.com/Leonardtown.dx6063192)[Hotels in Leonardtown](https://expedia.com/Leonardtown-Hotels.d6063192.Travel-Guide-Hotels)[Vacation Rentals in Leonardtown](https://expedia.com/Leonardtown-Vacation-Rentals.d6063192.Travel-Guide-VacationRentals)[Flights to Leonardtown](https://expedia.com/Cheap-Flights-To-Leonardtown.d6063192.Travel-Guide-Flights)[Car Rentals in Leonardtown](https://expedia.com/Car-Rentals-In-Leonardtown.d6063192.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6063192/34be8beb-743c-4949-9301-c65025c8bc39.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Leonardtown Vacations from $370 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Leonardtown Vacation The rich history and coastal scenery are just the start of the things Leonardtown has to offer. Discover the best parts of this captivating city your way with a customized Leonardtown vacation package. A trip to Leonardtown is a terrific opportunity to see the sights. Be sure to look around big-name attractions such as [St. Marys River State Park](https://www.expedia.com/St-Marys-River-State-Park-Maryland.d553248621561182375.Vacation-Attraction), [Port of Leonardtown Winery](https://www.expedia.com/Port-Of-Leonardtown-Winery-Leonardtown.d553248621532662050.Vacation-Attraction) and [New Towne Neck State Park](https://www.expedia.com/New-Towne-Neck-State-Park-Leonardtown.d637198023585345536.Vacation-Attraction). Whoever you're traveling with and whatever your bank balance, your ultimate Leonardtown vacation is just a few clicks away with Expedia. ## The Latest Leonardtown vacation packages Price found within the past 48 hours. Click for updated prices. ![YOTEL Washington DC](https://images.trvl-media.com/lodging/1000000/20000/10600/10576/04246907_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### YOTEL Washington DC Northwest Save 100% on your flight $370 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 8.2/10 Very Good! (2,307 reviews) Nice clean hotel, however room a little small and unusual with shower opening into the room. Location good for Capitol hill, bit further for Smithsonian, Lincoln memorial etc, but easily walkable. Staff were hit and miss, when we first arrived to drop bags the lady was rude, however when we came back to check-in the 2 gentlemen who helped us were both excellent. Reviewed on Mar 30, 2026 ![Beacon Hotel & Corporate Quarters](https://images.trvl-media.com/lodging/1000000/10000/7100/7069/0681397f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Beacon Hotel & Corporate Quarters Downtown Washington D.C. Save 100% on your flight $378 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 7.6/10 Good! (1,027 reviews) The check in was easy and the room was amazing. I loved the shower and bathroom. Staff were friendly and helpful. Reviewed on Mar 29, 2026 ![Arlo Washington DC](https://images.trvl-media.com/lodging/107000000/106090000/106087200/106087178/8cf67881_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Washington DC Northwest Save 100% on your flight $384 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 9.4/10 Exceptional! (1,340 reviews) Excellent experience! Onsite restaurants were both fantastic, friendly staff and he location could not have been better! Reviewed on Mar 29, 2026 ![Placemakr Buzzard Point](https://images.trvl-media.com/lodging/114000000/113170000/113163000/113162985/4d19de4c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Placemakr Buzzard Point Southwest Save 100% on your flight $686 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 9.2/10 Wonderful! (157 reviews) The room was very nice and clean. It made me want to stay longer. Love the view especially floor to ceiling windows. Couldn’t have asked for better accommodations. We will be returning to this location. Reviewed on Mar 30, 2026 ![Kellogg Conference Hotel at Gallaudet University](https://images.trvl-media.com/lodging/1000000/560000/552000/551972/a151aab7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kellogg Conference Hotel at Gallaudet University Northeast Save 100% on your flight $419 per person Jun 5 - Jun 8 found 1 day ago Roundtrip flight included Boston (BOS) to Washington (DCA) 8.2/10 Very Good! (1,001 reviews) Clean room and very friendly helpful staff Reviewed on Mar 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Leonardtown [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=DCA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Leonardtown #### Port of Leonardtown Winery You can enjoy a tasting or tour at Port of Leonardtown Winery during your travels to Leonardtown. Amble around this family-friendly area's riverfront or attend a sporting event. [](https://expedia.com/Port-Of-Leonardtown-Winery-Leonardtown.d553248621532662050.Vacation-Attraction) ## Leonardtown Hotel Deals ![The Inn at Leonardtown, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/3000000/2670000/2668800/2668771/5478a544_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Inn at Leonardtown, an Ascend Collection Hotel 41655 Park Avenue Leonardtown MD Fully refundable $130 nightly $145 total Apr 30 - May 1 Total with taxes and fees 9.4/10 Exceptional! (171 reviews) Great place to stay with nearby restaurants. Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F30%2F2026&endDate=5%2F1%2F2026&selected=2668771&PinnedHotelID=2668771&HadPinnedHotel=true®ionId=6063192) ![avid hotel California - Lexington Park by IHG](https://images.trvl-media.com/lodging/119000000/118640000/118639700/118639639/08bcaeff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### avid hotel California - Lexington Park by IHG 23274 Three Notch Road California MD Fully refundable $108 nightly $120 total Apr 2 - Apr 3 Total with taxes and fees 9/10 Wonderful! (38 reviews) The staff was WONDERFUL. I cannot say enough about how helpful and kind everyone was. The property itself is nice, but I did not read carefully enough that there was no refrigerator. This will likely deter me from staying here in the future. The other challenge was that the compressor in our hotel ... Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F2%2F2026&endDate=4%2F3%2F2026&selected=118639639&PinnedHotelID=118639639&HadPinnedHotel=true®ionId=6063192) ![Comfort Inn & Suites Lexington Park near Pax River](https://images.trvl-media.com/lodging/6000000/5100000/5098400/5098394/11804ad4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Lexington Park near Pax River 21885 Three Notch Rd Lexington Park MD Fully refundable $102 nightly $113 total Apr 29 - Apr 30 Total with taxes and fees 8.6/10 Excellent! (683 reviews) Clean room, friendly staff Reviewed on Mar 29, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F29%2F2026&endDate=4%2F30%2F2026&selected=5098394&PinnedHotelID=5098394&HadPinnedHotel=true®ionId=6063192) [See all 567 properties in Leonardtown](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F31%2F2026&endDate=4%2F1%2F2026®ionId=6063192) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Find the Best Leonardtown Vacation Packages ## Leonardtown Essential Information | Language | English | | --------------- | -------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 3,600 | | Max Temp Winter | 45ºF | | Max Temp Summer | 85ºF | | Top Sights | [St. Marys River State Park](https://www.expedia.com/St-Marys-River-State-Park-Maryland.d553248621561182375.Vacation-Attraction), [Port of Leonardtown Winery](https://www.expedia.com/Port-Of-Leonardtown-Winery-Leonardtown.d553248621532662050.Vacation-Attraction) and [Jefferson Patterson Park and Museum](https://www.expedia.com/Jefferson-Patterson-Park-And-Museum-St-Leonard.d553248621532662081.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Leonardtown vacation package cost? ### What are the cheapest months to go to Leonardtown? ### How many days is enough for Leonardtown? ### How to find the best Leonardtown package deals? ### Is it cheaper to book a Leonardtown vacation as a package? ### When to book a vacation package to Leonardtown? ### Does Expedia offer Book Now, Pay Later Leonardtown vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app