Book Holiday Homes in St. Leonard

Start date: Check-in selected.
To Date
End date: Check-out

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

4BDRM River front house with Private Beach in Hollywood

4BDRM River front house with Private Beach in Hollywood

2 out of 5
Hollywood
When you stay at this vacation home in Hollywood, you'll be on the beach and 6 minutes by car from Greenwell State Park.
Opens in a new window4BDRM River front house with Private Beach in Hollywood
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Cobb Island
When you stay at this vacation home in Cobb Island, you'll be on the waterfront and steps from Potomac River.
Opens in a new windowWaterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Single family home with screened porch.

Single family home with screened porch.

Fishing Creek
Located in Fishing Creek, this vacation home is a 1-minute drive from P. L. Jones Marina and 6 minutes from Gunners Island.
Opens in a new windowSingle family home with screened porch.
Save an average of 15% on thousands of hotels when you're signed in
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville
With a stay at this vacation home in Mechanicsville, you'll be within a 15-minute drive of John Baggett Park at Laurel Grove and Laurel Ridge Park.
Opens in a new windowSecluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is AU$691 per night from 1 Oct to 2 Oct
AU$691
1 Oct - 2 Oct
includes taxes & fees
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Ragged Island.
Opens in a new windowBeautiful Waterfront Retreat in Cambridge!
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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

North Beach
Located in Owings, this vacation home is a 3-minute drive from Bayside History Museum and 6 minutes from Chesapeake Beach Water Park.
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
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 beach, and 5.2 mi (8.3 km) from Dennis Point Marina and 7.7 mi (12.4 km) from Cecil's Old ...
Opens in a new windowSpacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby
Located in Lusby, this vacation home is on a lake, within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Opens in a new windowBay view from Calvert Cliffs, Solomons Island & State Park nearby
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
When you stay at this vacation home in Lusby, you'll be within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Opens in a new windowBelle of the Chesapeake Bay
Don't see what you're looking for?
See all available properties in St. Leonard
View all properties
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
237 Holiday Homes
Lowest Price
AU$206
Highest Price
AU$691
Popular accommodation
4BDRM River front house with Private Beach in Hollywood, Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River, Single family home with screened porch. , Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More, Beautiful Waterfront Retreat in Cambridge!, The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Belle of the Chesapeake Bay

Top trending hotels in St. Leonard

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.
Opens in a new windowWATERFRONT!!! The River's Roost on The Patuxent River
Summer Getaway ~ Beach Combing & Relaxation

Summer Getaway ~ Beach Combing & Relaxation

St Leonard
When you stay at this vacation home in St. Leonard, you'll be near the beach, within a 15-minute walk of Matoaka Beach and Long Beach.
Opens in a new windowSummer Getaway ~ Beach Combing & Relaxation
Studio on the Bay.

Studio on the Bay.

Saint Leonard
When you stay at this apartment in St. Leonard, you'll be near the beach, within a 10-minute walk of Flag Ponds Nature Park and Flag Harbor Marina.
Opens in a new windowStudio on the Bay.
Save an average of 15% on thousands of hotels when you're signed in
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 2 Oct to 3 Oct
AU$206
2 Oct - 3 Oct
includes taxes & fees
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be a 3-minute walk from Southern Branch Library and 11 minutes by foot from Drum Point ...
Opens in a new windowSolomons Inn Resort & Marina
Don't see what you're looking for?
See all available properties in St. Leonard
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.