Book Holiday Homes in St. Leonard

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Featured Holiday Homes in St. Leonard

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage

North Beach MD
With a stay at this vacation home in North Beach, you'll be steps from Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window"La Licorne" Waterfront Beach Cottage
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

North Beach MD
With a stay at this vacation home in Owings, you'll be within a 5-minute drive of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
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Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.

Montross VA
When you stay at this vacation home in Montross, you'll be on the waterfront and 15 minutes by car from Hague Winery.
Opens in a new windowThe Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach MD
When you stay at this vacation home in North Beach, you'll be by the sea, within a 10-minute walk of Chesapeake Bay and Bayside History Museum.
Opens in a new windowThe Blue Crab Beach House - Free beach passes
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Lusby MD
With a stay at this vacation home in Lusby, you'll be on a lake, within a 10-minute drive of Chesapeake Bay and Cove Point Park.
Opens in a new windowBay view from Calvert Cliffs, Solomons Island & State Park nearby
All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21

All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21

Hague VA
Located in Hague, this vacation home is on the waterfront, within a 15-minute drive of Coles Point Marina and Hague Winery.
Opens in a new windowAll Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21
Back Creek Villa Covered Deck

Back Creek Villa Covered Deck

Solomons MD
With a stay at this vacation home in Solomons Island, you'll be within a 15-minute drive of Chesapeake Bay and J.C. Lore Oyster House.
Opens in a new windowBack Creek Villa Covered Deck
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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.

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
226 Holiday Homes
Lowest Price
AU$223
Highest Price
AU$223
Popular accommodation
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, "La Licorne" Waterfront Beach Cottage, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach., The Blue Crab Beach House - Free beach passes , Bay view from Calvert Cliffs, Solomons Island & State Park nearby, All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21, Back Creek Villa Covered Deck

Top trending hotels in St. Leonard

Beach Combing & Relaxation

Beach Combing & Relaxation

St Leonard MD
When you stay at this vacation home in St. Leonard, you'll be near the beach, within a 10-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowBeach Combing & Relaxation
WATERFRONT!!! The River's Roost on The Patuxent River

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

Saint Leonard MD
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Gray's Road Dog Park and Battle Creek Cypress Swamp Sanctuary.
Opens in a new windowWATERFRONT!!! The River's Roost on The Patuxent River
Cottage on the Bay

Cottage on the Bay

Saint Leonard MD
With a stay at this cottage in St. Leonard, you'll be a 1-minute walk from Chesapeake Bay and 6 minutes by foot from Flag Ponds Nature Park.
Opens in a new windowCottage on the Bay
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Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is AU$223 per night from 25 May to 26 May
AU$223
25 May - 26 May
includes taxes & fees
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and Rod n Reel Charter ...
Opens in a new windowRod 'N' Reel Resort
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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.

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^Subject to availability and chosen travel dates.