Book Holiday Homes in Leonardtown

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Featured Holiday Homes in Leonardtown

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!
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 Cardinal Gibbons Park.
Waterfront Scotland Beach Retreat w/ Private Beach
Waterfront Relaxing Getaway

Waterfront Relaxing Getaway

Coltons Point
When you stay at this vacation home in Coltons Point, you'll be on the waterfront and 6 minutes by foot from St. Clement's Island State Park.
Waterfront Relaxing Getaway
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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
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
When you stay at this vacation home in Hague, you'll be on the beach and 14 minutes by car from Hague Winery.
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat

Lusby
Located in Lusby, this vacation home is on the waterfront, within a 15-minute drive of Calvert Cliffs State Park and Annmarie Sculpture Garden and Arts ...
Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC

Mechanicsville
When you stay at this vacation home in Mechanicsville, you'll be on the waterfront and within a 5-minute drive of Cape Saint Marys Marina.
Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC
Picture Perfect  Waterfront in town  Sleeps 6  Expansive Outdoor dining area

Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area

Colonial Beach
A stay at this vacation home places you in the heart of Colonial Beach, within a 10-minute walk of Bayside Marina and Colonial Beach.
Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area
Spectacular Waterfront Retreat with Pier

Spectacular Waterfront Retreat with Pier

Newburg
When you stay at this vacation home in Newburg, you'll be on the waterfront and 14 minutes by car from Potomac River.
Spectacular Waterfront Retreat with Pier
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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
201 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$195
Popular accommodation
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Waterfront Scotland Beach Retreat w/ Private Beach, Waterfront Relaxing Getaway, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! , Stunning Water Front Home 90 minutes from DC with Deepwater Dock.Bring your boat, Stylish & Modern Waterfront retreat, Serene and with great views,1Hr to DC, Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area, Spectacular Waterfront Retreat with Pier

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$195 per night from 5 Jan to 6 Jan
AU$195
includes taxes & fees
5 Jan - 6 Jan 2025
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
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$180 per night from 26 Dec to 27 Dec
AU$180
includes taxes & fees
26 Dec - 27 Dec
Located in Prince Frederick, Springhill Suites by Marriott Prince Frederick is within a 10-minute drive of Running Hare Vineyard and Patuxent River.
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$162 per night from 25 Dec to 26 Dec
AU$162
includes taxes & fees
25 Dec - 26 Dec
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of Patuxent River Naval Air Museum and Patuxent ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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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$116 per night from 3 Jan to 4 Jan
AU$116
includes taxes & fees
3 Jan - 4 Jan 2025
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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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.