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

Leonardtown Vacations from $279

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The Latest Leonardtown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Oct 1 - Oct 4

    Lord Baltimore Hotel + Flight

    Downtown Baltimore
    3 nights
    3.5 star property
    8.4/10 - Very Good (3,008 reviews)
    "I"
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    Save 100% on your flight
    $451
    $279
    per traveler
    found 1 day ago
    Lord Baltimore Hotel
  • 2 restaurants; breakfast and dinner served
    Oct 2 - Oct 5

    Hotel Burg + Flight

    Leesburg's Old and Historic District
    3 nights
    4.0 star property
    9.6/10 - Exceptional (95 reviews)
    "Amazing experience"
    Reviewed July 12, 2026
    Roundtrip • Boston (BOS) - Baltimore (BWI)
    BOS - BWI • Nonstop BWI - BOS • Nonstop
    Save 100% on your flight
    $1,674
    $1,005
    per traveler
    found 0 hours ago
    Hotel Burg
  • Interior detail
    Oct 4 - Oct 10

    The River Inn + Flight

    Northwest
    6 nights
    4.0 star property
    9.4/10 - Exceptional (2,031 reviews)
    "Clean and specious rooms. Perfect for my family of 5."
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - DCA • Nonstop DCA - ATL • Nonstop
    Save 100% on your flight
    $1,142
    $713
    per traveler
    found 1 day ago
    The River Inn
  • Terrace/patio
    Sep 3 - Sep 7

    Kellogg Conference Hotel at Gallaudet University + Flight

    Northeast
    4 nights
    3.0 star property
    8.2/10 - Very Good (1,000 reviews)
    "The stay wasn’t great at all. We had very noisy neighbours. When we called the reception the first time, they said they would take care of it, but no one did. We called the second time, then someone came and knocked on our door first to confirm that it was us that called, which is unprofessional. It sounded like he talked to the noisy neighbours. Nothing changed. We had just enough after and had to bang on the wall and yell for the neighbours to stop. After that, they were quiet. After we got..."
    Reviewed July 13, 2026
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - BWI • Nonstop BWI - ATL • Nonstop
    Save 100% on your flight
    $528
    $330
    per traveler
    found 1 day ago
    Kellogg Conference Hotel at Gallaudet University
  • Dining
    Oct 4 - Oct 10

    Phoenix Park Hotel + Flight

    Northwest
    6 nights
    3.5 star property
    9.4/10 - Exceptional (2,181 reviews)
    "Good"
    Reviewed July 18, 2026
    Roundtrip • Atlanta (ATL) - Baltimore (BWI)
    ATL - DCA • Nonstop DCA - ATL • Nonstop
    Save 100% on your flight
    $1,165
    $730
    per traveler
    found 1 day ago
    Phoenix Park Hotel

Discover the most popular places to visit in Leonardtown

Leonardtown Town Hall

This historic building serves as the heart of Leonardtown's civic operations and community gatherings. Combine your visit with a stroll through the charming downtown area to experience local culture.

Leonardtown Hotel Deals

Lobby

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel
2.5 star property
< 0.1 mi from Leonardtown
9.4 out of 10, Exceptional, (181 reviews)
"This hotel is very cute, clean and centrally located to the downtown Leonardtown area. Parking was very accessible and easy and I loved that breakfast was included. My only issue was the woman working at the front desk when we checked in. She was grumpy and not very friendly. We arrived at noon so we understood it was early and that all of our rooms might not yet be ready, but she seemed annoyed at us! And didn’t offer any accommodations to help us settle in after a 7 hour drive."
$143 nightly
The price is $159
Aug 13 - Aug 14
Total with taxes and fees
The Inn at Leonardtown, an Ascend Collection Hotel
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.
See all properties in Leonardtown

Frequently Asked Questions

How much does a Leonardtown vacation package cost?

You can grab a vacation package to this top destination from $279 on Expedia. But how much your vacation to Leonardtown costs will depend on the season, length of stay and hotel choice.

What are the cheapest months to go to Leonardtown?

You can typically find reduced prices and greater availability in January, February and August. Explore our cheap Leonardtown vacation packages and you could score some great off-season discounts.

How many days is enough for Leonardtown?

With a well-organized itinerary, you can easily hit the top Leonardtown sights in a handful of days. But if you prefer to venture off the beaten track or take day trips, think about booking your Leonardtown vacation for longer.

How to find the best Leonardtown package deals?

Finding a cheap Leonardtown package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Leonardtown package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.

Is it cheaper to book a Leonardtown vacation as a package?

An Expedia vacation package could score you significant savings when compared to arranging flights and stays separately. Better still, you can personalize your Leonardtown getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.

When to book a vacation package to Leonardtown?

Land fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Leonardtown trip.

Does Expedia offer Book Now, Pay Later Leonardtown vacation packages?

Your Leonardtown break is meant to be an escape from your busy life, not a source of money-related stress. So to give you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.