Book Holiday Homes in Leonardtown

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Featured Holiday Homes in Leonardtown

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!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach Cottage, 7 minutes walk to beach!

Colonial Beach
A stay at this vacation home places you in the heart of Colonial Beach, within a 15-minute walk of Colonial Beach and Colonial Beach Historical Society.
Colonial Beach Cottage, 7 minutes walk to beach!
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Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks

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 Cardinal Gibbons Park.
Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks
Hawthorn House Remodeled 3BR Walk to Town!

Hawthorn House Remodeled 3BR Walk to Town!

Colonial Beach
With a stay at this vacation home in Colonial Beach, you'll be within a 5-minute walk of Colonial Beach Historical Society and Colonial Beach.
Hawthorn House Remodeled 3BR Walk to Town!
Sea Glass Beach House!  Large sand beach, dock and hot tub! Pets welcome!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague
Located in Hague, this vacation home is by the ocean, within a 15-minute drive of Coles Point Marina and Hague Winery.
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

Lusby
Located in Lusby, this vacation home is by the ocean, a 4-minute drive from Drum Point Lake and 5 minutes from Seahorse Beach.
Waterfront Lusby Retreat w/ Deep-Water Dock & Slip
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.
Belle of the Chesapeake Bay
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
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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
207 Holiday Homes
Lowest Price
AU$120
Highest Price
AU$250
Popular accommodation
Screened Patio, Deck & Grill: Saint Inigoes Home!, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Colonial Beach Cottage, 7 minutes walk to beach!, Beach Cottage With A Spectacular View ~ Your Own Private Beach ~ Includes Kayaks, Hawthorn House Remodeled 3BR Walk to Town!, Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! , Waterfront Lusby Retreat w/ Deep-Water Dock & Slip, Belle of the Chesapeake Bay, Inviting and Serene Home on Monroe Bay Creek

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$192 per night from 2 Mar to 3 Mar
AU$192
includes taxes & fees
2 Mar - 3 Mar
A stay at The Inn at Leonardtown, Ascend Hotel Collection places you in the heart of Leonardtown, steps from Leonardtown Town Hall and 11 minutes by foot from ...
The Inn at Leonardtown, Ascend Hotel Collection
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

3 out of 5
75 Sherry Lane, Prince Frederick, MD
The price is AU$250 per night from 16 Mar to 17 Mar
AU$250
includes taxes & fees
16 Mar - 17 Mar
With a stay at Springhill Suites by Marriott Prince Frederick in Prince Frederick, you'll be a 1-minute walk from R&J's PlayPark and 7 minutes by foot from calvART ...
Springhill Suites by Marriott Prince Frederick
Red Roof Inn Dahlgren - Naval Base

Red Roof Inn Dahlgren - Naval Base

2 out of 5
4661 James Madison Pkwy, King George, VA
Fully refundableReserve now, pay when you stay
The price is AU$120 per night from 2 Mar to 3 Mar
AU$120
includes taxes & fees
2 Mar - 3 Mar
With a stay at Red Roof Inn Dahlgren - Naval Base in King George, you'll be within a 10-minute drive of Aqualand Marina and Potomac River.
Red Roof Inn Dahlgren - Naval Base
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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$162 per night from 2 Mar to 3 Mar
AU$162
includes taxes & fees
2 Mar - 3 Mar
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
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.