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!
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 Battle Creek Cypress Swamp Sanctuary.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
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
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
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
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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
204 Holiday Homes
Lowest Price
AU$164
Highest Price
AU$206
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!, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Inviting and Serene Home on Monroe Bay Creek, Belle of the Chesapeake Bay, Waterfront Lusby Retreat w/ Deep-Water Dock & Slip

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$194 per night from 9 Feb to 10 Feb
AU$194
includes taxes & fees
9 Feb - 10 Feb
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
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 27 Jan to 28 Jan
AU$206
includes taxes & fees
27 Jan - 28 Jan
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
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$164 per night from 25 Jan to 26 Jan
AU$164
includes taxes & fees
25 Jan - 26 Jan
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of San Souci Shopping Center and Dunleigh Neighborhood ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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My Place Hotel - Dahlgren/King George, VA

My Place Hotel - Dahlgren/King George, VA

2.5 out of 5
4235 Market Center Drive, King George, VA
Fully refundableReserve now, pay when you stay
The price is AU$174 per night from 23 Feb to 24 Feb
AU$174
includes taxes & fees
23 Feb - 24 Feb
Located in King George, My Place Hotel - Dahlgren/King George, VA is within a 10-minute drive of Aqualand Marina and Potomac River.
My Place Hotel - Dahlgren/King George, VA
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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.