Book Holiday Homes in St. Leonard
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 St. Leonard

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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

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

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

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families
St. Leonard 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 St. Leonard vacation homes are the perfect way for you to wing it.
Holiday houses in St. Leonard 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 St. Leonard 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 St. Leonard adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in St. Leonard 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 St. Leonard 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.
St. Leonard Holiday Homes essential information
Accommodation | 217 Holiday Homes |
|---|---|
Lowest Price | NZ$238 |
Highest Price | NZ$670 |
Popular accommodation | The Cozy Crab- Your Charming Haven in Lovely North Beach!, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, 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 , Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space., Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families |
Top trending hotels in St. Leonard

Summer Getaway ~ Beach Combing & Relaxation

Discover tranquility near Calvert Cliffs

WATERFRONT!!! The River's Roost on The Patuxent River

Rod 'N' Reel Resort
More ways to explore St. Leonard
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.
