Book Holiday Homes in Leonardtown

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Featured Holiday Homes in Leonardtown

Inviting and Serene Home on Monroe Bay Creek

Inviting and Serene Home on Monroe Bay Creek

Colonial Beach
When you stay at this vacation home in Colonial Beach, you'll be on the waterfront, within a 5-minute drive of James Monroe Birthplace and Monrovia.
Inviting and Serene Home on Monroe Bay Creek
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 Calvert Cliffs State Park and Patuxent River.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel

Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel

Lottsburg
With a stay at this vacation home in Lottsburg, you'll be on the waterfront, and 10 mi (16.1 km) from Heathsville Farmers' Market and 10 mi (16.1 km) from Rice's ...
Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel
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Waterfront Scotland Beach Retreat w/Private Beach!

Waterfront Scotland Beach Retreat w/Private Beach!

Ridge
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Confederate Memorial Park and Point Lookout State Park.
Waterfront Scotland Beach Retreat w/Private Beach!
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**

Ridge
With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Confederate Memorial Park and Point Lookout State Park.
**FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**
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
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.
Waterfront House with Dock, Kayaks, & Sailboat!

Waterfront House with Dock, Kayaks, & Sailboat!

California
With a stay at this vacation home in California, you'll be on the waterfront, within a 15-minute drive of Patuxent River Naval Air Station and Patuxent ...
Waterfront House with Dock, Kayaks, & Sailboat!
The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.

The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.

Colonial Beach
When you stay at this vacation home in Colonial Beach, you'll be near the beach, within a 5-minute drive of Colonial Beach Historical Society and Colonial ...
The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.
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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.

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
173 Holiday Homes
Lowest Price
AU$86
Highest Price
AU$203
Popular accommodation
Inviting and Serene Home on Monroe Bay Creek, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Waterfront, hot tub, screen porch, kayaks, SUP, pier fishing, private feel, Waterfront Scotland Beach Retreat w/Private Beach!, **FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS**, Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp, The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach., Waterfront House with Dock, Kayaks, & Sailboat!, The Blue Crab is 5 blocks from Beach, 0.5 miles to Beach, 100 ft from bay.

Top trending hotels in Leonardtown

The Inn at Leonardtown, Ascend Hotel Collection

The Inn at Leonardtown, Ascend Hotel Collection

2.5 out of 5
41655 Park Avenue, Leonardtown, MD
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 2 Jun to 3 Jun
AU$203
per night
2 Jun - 3 Jun
A stay at The Inn at Leonardtown, Ascend Hotel Collection places you in the heart of Leonardtown, a 4-minute drive from Port of Leonardtown Winery and 10 minutes ...
The Inn at Leonardtown, Ascend Hotel Collection
River Edge Inn

River Edge Inn

2.5 out of 5
30 Colonial Ave, Colonial Beach, VA
Fully refundableReserve now, pay when you stay
The price is AU$170 per night from 19 May to 20 May
AU$170
per night
19 May - 20 May
Located in Colonial Beach, River Edge Inn is on the Strip, a 1-minute drive from Colonial Beach and 13 minutes from Ingleside Vineyards.
River Edge Inn
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is AU$139 per night from 19 May to 20 May
AU$139
per night
19 May - 20 May
With a stay at La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent in California, you'll be within a 5-minute drive of Patuxent River Naval Air Station ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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Prince Frederick

Prince Frederick

3 out of 5
75 Main St, Prince Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$86 per night from 24 May to 25 May
AU$86
per night
24 May - 25 May
With a stay at Prince Frederick in Prince Frederick, you'll be within a 10-minute drive of Running Hare Vineyard and Battle Creek Cypress Swamp Sanctuary.
Prince Frederick
Don't see what you're looking for?
See all available properties in Leonardtown
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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.