Book Holiday Homes in Leonardtown
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Leonardtown

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Shewell's A-Frame on Mill Creek

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Discover tranquility near Calvert Cliffs

Waterfront with spectacular view, close to restaurants and bars

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Inviting and Serene Home on Monroe Bay Creek

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Leonardtown Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Leonardtown vacation homes are the perfect way for you to wing it.
Holiday houses in Leonardtown let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Leonardtown in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Leonardtown adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Leonardtown with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Leonardtown vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Leonardtown Holiday Homes essential information
Accommodation | 243 Holiday Homes |
|---|---|
Lowest Price | NZ$160 |
Highest Price | NZ$677 |
Popular accommodation | 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Shewell's A-Frame on Mill Creek, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Discover tranquility near Calvert Cliffs , Waterfront with spectacular view, close to restaurants and bars, Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons, Inviting and Serene Home on Monroe Bay Creek, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space., Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp |
Top trending hotels in Leonardtown

The Inn at Leonardtown, an Ascend Collection Hotel

My Place Hotel - Dahlgren/King George, VA

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Solomons Inn Resort & Marina
More ways to explore Leonardtown
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
