Book Holiday Homes in Leonardtown
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Featured Holiday Homes in Leonardtown
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.
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.
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.
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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 ...
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.
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.
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.
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.
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.
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
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 ...
avid hotel California - Lexington Park by IHG
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 ...
Comfort Inn & Suites Lexington Park near Pax River
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 ...
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My Place Hotel - Dahlgren/King George, VA
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.
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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**Terms and Conditions apply.
^Subject to availability and chosen travel dates.