Leonardtown Vacations from $354
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The Latest Leonardtown Vacation Packages
- Arlo Washington DC
Sep 25 - Sep 28Arlo Washington DC + Flight
Northwest3 nights4.0 star property9.4/10 - Exceptional (1,844 reviews)"Staying at the Arlo was top notch from beginning to end! The unique treats of colorful fortune cookies greeting each of us was welcoming. The hotel staff did a fantastic job keeping the room pristine! Breakfast was wonderful and accommodated everyone well with our variety of tastes. The location of the hotel was within walking distance to all of the historical sites we wanted to see while staying there."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Hotel Burg
Sep 9 - Sep 14Hotel Burg + Flight
Leesburg's Old and Historic District5 nights4.0 star property9.6/10 - Exceptional (102 reviews)Roundtrip • Dallas (DFW) - Baltimore (BWI)DFW - BWI • Nonstop BWI - DFW • 1 stop - Eurostars Saint Gregory Dupont Circle Georgetown
Oct 10 - Oct 14Eurostars Saint Gregory Dupont Circle Georgetown + Flight
Downtown Washington D.C.4 nights4.0 star property8.8/10 - Excellent (1,002 reviews)"I highly recommend. This is a nice hotel, with a affordable luxury vibe. Room lighting, furniture, and layout were great. Very clean. Staff were very helpful and efficient. Fitness room was a little bigger and better equipped than most at this price point. My only minor complaint is that the TV Google Chromecast wouldn't work (I use Chromecast regularly...I think the TV may have been on a different network than the guest wifi). All said, I will likely stay here again for my periodic business..."Reviewed July 30, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - Comfort Inn & Suites Baltimore Inner Harbor
Oct 2 - Oct 6Comfort Inn & Suites Baltimore Inner Harbor + Flight
Downtown Baltimore4 nights3.0 star property5.2/10 - (1,000 reviews)"Dirty, run down, smelly, old and broken fixtures, stay away at all cost"Reviewed July 28, 2026Roundtrip • Dallas (DFW) - Baltimore (BWI)DFW - BWI • Nonstop BWI - DFW • Nonstop - Phoenix Park Hotel
Sep 3 - Sep 7Phoenix Park Hotel + Flight
Northwest4 nights3.5 star property9.4/10 - Exceptional (2,181 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop
Discover the most popular places to visit in Leonardtown
Leonardtown Hotel Deals
The Inn at Leonardtown, an Ascend Collection Hotel
The Inn at Leonardtown, an Ascend Collection Hotel
Historic 1825 Chesapeake Farm Stay
Historic 1825 Chesapeake Farm Stay
avid hotel California - Lexington Park by IHG
avid hotel California - Lexington Park by IHG
Spark by Hilton California Lexington Park
Spark by Hilton California Lexington Park
Sleep Inn & Suites California MD
Sleep Inn & Suites California MD
Holiday Inn Express & Suites Lexington Park-California by IHG
Holiday Inn Express & Suites Lexington Park-California by IHG
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
La Quinta Inn & Suites by Wyndham Lexington Park - PatuxentFrequently Asked Questions
How much does a Leonardtown vacation package cost?
You can grab a vacation package to this top destination from $354 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.