Book Holiday Homes in Leonardtown

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 Leonardtown

Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Seahorse Beach.
Waterfront Wildlife Retreat on the Patuxent River
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.
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
Save an average of 15% on thousands of hotels when you're signed in
House Right on the Potomac River - Great Sunrises & Sunsets

House Right on the Potomac River - Great Sunrises & Sunsets

Hague
Located in Hague, this vacation home is on the waterfront, within a 15-minute drive of Coles Point Marina and Hague Winery.
House Right on the Potomac River - Great Sunrises & Sunsets
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 calvART Gallery.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
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
Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Beachy Maryland A-Frame: Steps to Chesapeake Bay!

Scotland
Located in Scotland (Point Lookout), this vacation home is within a 5-minute drive of Confederate Memorial Park and Lake Conoy.
Beachy Maryland A-Frame: Steps to Chesapeake Bay!
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!
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

Colonial Beach
Located in Colonial Beach, this vacation home is within a 5-minute drive of James Monroe Birthplace and Monrovia.
1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit
Don't see what you're looking for?
See all available properties in Leonardtown
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.

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
265 Holiday Homes
Lowest Price
AU$161
Highest Price
AU$217
Popular accommodation
Waterfront Wildlife Retreat on the Patuxent River , The Beach Retreat is a cozy beach Villa with Hottub overlooking a private beach., Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp, House Right on the Potomac River - Great Sunrises & Sunsets, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Picture Perfect Waterfront in town Sleeps 6 Expansive Outdoor dining area, Beachy Maryland A-Frame: Steps to Chesapeake Bay!, Screened Patio, Deck & Grill: Saint Inigoes Home!, 1 Mi to Colonial Beach Boardwalk: Home w/ Fire Pit

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$214 per night from 18 May to 19 May
AU$214
includes taxes & fees
18 May - 19 May
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
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$194 per night from 13 May to 14 May
AU$194
includes taxes & fees
13 May - 14 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
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$217 per night from 27 Apr to 28 Apr
AU$217
includes taxes & fees
27 Apr - 28 Apr
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be within a 15-minute drive of Patuxent River Naval Air Station and Southern Branch Library.
Solomons Inn Resort & Marina
Save an average of 15% on thousands of hotels when you're signed in
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$161 per night from 21 Apr to 22 Apr
AU$161
includes taxes & fees
21 Apr - 22 Apr
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
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.