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Featured Holiday Homes in Leonardtown

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR

Lusby MD
Located in Lusby, this vacation home is a 5-minute drive from Chesapeake Bay and 6 minutes from Chesapeake Hills Golf Course.
Opens in a new windowMid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby MD
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Chesapeake Bay.
Opens in a new windowWaterfront Wildlife Retreat on the Patuxent River
Back Creek Villa Covered Deck

Back Creek Villa Covered Deck

Solomons MD
With a stay at this vacation home in Solomons Island, you'll be just steps from Solomons Island Boardwalk and J.C. Lore Oyster House.
Opens in a new windowBack Creek Villa Covered Deck
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The Pearl - Waterfront Retreat  • 4BR • 7 Bed ��• Family / Friends / Pets

The Pearl - Waterfront Retreat • 4BR • 7 Bed • Family / Friends / Pets

Colonial Beach VA
With a stay at this vacation home in Colonial Beach, you'll be a 5-minute walk from Colonial Beach and 13 minutes by foot from Colonial Beach Historical ...
Opens in a new windowThe Pearl - Waterfront Retreat • 4BR • 7 Bed • Family / Friends / Pets
Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More

Mechanicsville MD
With a stay at this vacation home in Mechanicsville, you'll be within a 15-minute drive of John Baggett Park at Laurel Grove and Laurel Ridge Park.
Opens in a new windowSecluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More
Quaint waterfront home with private beach

Quaint waterfront home with private beach

Montross VA
When you stay at this vacation home in Montross, you'll be on the beach and 14 minutes by car from Hague Winery.
Opens in a new windowQuaint waterfront home with private beach
Shewell's A-Frame on Mill Creek

Shewell's A-Frame on Mill Creek

Lusby MD
Located in Lusby, this vacation home is within a 5-minute drive of Drum Point Lake and Chesapeake Bay.
Opens in a new windowShewell's A-Frame on Mill Creek
A breathtaking secluded luxury waterfront cottage, complete with a private pier.

A breathtaking secluded luxury waterfront cottage, complete with a private pier.

Lusby MD
Located in Lusby, this vacation home is on the waterfront, within a 10-minute drive of Calvert Cliffs State Park and Drum Point Lake.
Opens in a new windowA breathtaking secluded luxury waterfront cottage, complete with a private pier.
Waterfront with spectacular view, close to restaurants and bars

Waterfront with spectacular view, close to restaurants and bars

Colonial Beach VA
When you stay at this vacation home in Colonial Beach, you'll be on the waterfront, within a 15-minute walk of Bayside Marina and Colonial Beach.
Opens in a new windowWaterfront with spectacular view, close to restaurants and bars
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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
243 Holiday Homes
Lowest Price
AU$121
Highest Price
AU$209
Popular accommodation
Mid-Century Modern Lake House – Gorgeous Fall Views, Fire pit, Sauna, 4BR, Waterfront Wildlife Retreat on the Patuxent River , Back Creek Villa Covered Deck, The Pearl - Waterfront Retreat • 4BR • 7 Bed • Family / Friends / Pets, Secluded Riverfront Retreat on 100+ Acre Farm in Mechanicsville, WiFi, AC, &More, Quaint waterfront home with private beach, Shewell's A-Frame on Mill Creek, A breathtaking secluded luxury waterfront cottage, complete with a private pier., Waterfront with spectacular view, close to restaurants and bars

Top trending hotels in Leonardtown

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

2.5 out of 5
41655 Park Avenue Leonardtown MD
Fully refundable
The price is AU$209 per night from 30 Apr to 1 May
AU$209
30 Apr - 1 May
includes taxes & fees
A stay at The Inn at Leonardtown, an Ascend Collection Hotel places you in the heart of Leonardtown, steps from Leonardtown Town Hall and 11 minutes by foot ...
Opens in a new windowThe Inn at Leonardtown, an Ascend Collection Hotel
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is AU$178 per night from 5 Apr to 6 Apr
AU$178
5 Apr - 6 Apr
includes taxes & fees
Located in California, avid hotel California - Lexington Park by IHG is in the historical district, within a 5-minute drive of Wildewood Shopping Center and ...
Opens in a new windowavid hotel California - Lexington Park by IHG
Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

2.5 out of 5
21885 Three Notch Rd Lexington Park MD
Fully refundable
The price is AU$166 per night from 29 Apr to 30 Apr
AU$166
29 Apr - 30 Apr
includes taxes & fees
Located in Lexington Park, Comfort Inn & Suites Lexington Park near Pax River is in the suburbs, within a 15-minute walk of Patuxent River Naval Air Station ...
Opens in a new windowComfort Inn & Suites Lexington Park near Pax River
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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$121 per night from 19 Apr to 20 Apr
AU$121
19 Apr - 20 Apr
includes taxes & fees
Located in King George, My Place Hotel - Dahlgren/King George, VA is within a 10-minute drive of Aqualand Marina and Potomac River.
Opens in a new windowMy 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.

Top Picks

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^Subject to availability and chosen travel dates.