Book Holiday Homes in St. Leonard

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Featured Holiday Homes in St. Leonard

The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Seahorse Beach.
Waterfront Wildlife Retreat on the Patuxent River
Modern Waterfront House with Amazing views!

Modern Waterfront House with Amazing views!

North Beach
Located in North Beach, this vacation home is on the waterfront, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
Modern Waterfront House with Amazing views!
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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
When you stay at this vacation home in Montross, you'll be on the waterfront and 15 minutes by car from Hague Winery.
The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach.
Sweet Bamboo Beach Cottage

Sweet Bamboo Beach Cottage

north beach
When you stay at this vacation home in North Beach, you'll be on the beach, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water ...
Sweet Bamboo Beach Cottage
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Drayden
With a stay at this vacation home in Drayden, you'll be on the waterfront, and 11.2 mi (18.1 km) from Patuxent River Naval Air Station and 5.2 mi (8.3 km) from ...
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
House Right on the Potomac River - Great Sunrises & Sunsets

House Right on the Potomac River - Great Sunrises & Sunsets

Hague
Located in Hague, this vacation home is on the waterfront, within a 15-minute drive of Coles Point Marina and Hague Winery.
House Right on the Potomac River - Great Sunrises & Sunsets
Stunning  Chesapeake view from almost ever room, private  15 home community beach, fossils, 450 pier

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

Port Republic
Located in Port Republic, this vacation home is on the waterfront, within a 10-minute drive of R&J's PlayPark and calvART Gallery.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!

St Inigoes
Located in Saint Inigoes, this vacation home is on the waterfront, a 3-minute drive from Saint Inigoes State Forest and 7 minutes from Cardinal Gibbons ...
Screened Patio, Deck & Grill: Saint Inigoes Home!
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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
222 Holiday Homes
Lowest Price
AU$246
Highest Price
AU$246
Popular accommodation
The Blue Crab Beach House - Free beach passes , Waterfront Wildlife Retreat on the Patuxent River , Modern Waterfront House with Amazing views!, The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach., Sweet Bamboo Beach Cottage, Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp, House Right on the Potomac River - Great Sunrises & Sunsets, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Screened Patio, Deck & Grill: Saint Inigoes Home!

Top trending hotels in St. Leonard

5 bedroom, 8 bed, 3 story house a block from beach

5 bedroom, 8 bed, 3 story house a block from beach

Saint Leonard
Located in St. Leonard, this vacation home is in a rural location, within a 15-minute walk of Flag Harbor Marina and Flag Ponds Nature Park.
5 bedroom, 8 bed, 3 story house a block from beach
WATERFRONT!!! The River's Roost on The Patuxent River

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

Saint Leonard
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.
WATERFRONT!!! The River's Roost on The Patuxent River
New! Cozy River Cottage with great views of the water!

New! Cozy River Cottage with great views of the water!

Saint Leonard
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and ...
New! Cozy River Cottage with great views of the water!
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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$246 per night from 21 Apr to 22 Apr
AU$246
includes taxes & fees
21 Apr - 22 Apr
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 3 minutes by foot ...
Rod '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.