Leonardtown Vacation Rentals

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Vacation Rentals in Leonardtown

Serenity by the Lake. Spacious lake house incredible views in Colonial Beach

Colonial Beach VA

Located in Colonial Beach, this vacation home is on the waterfront, within a 10-minute drive of Monrovia and James Monroe Birthplace.

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.

Peace & Tranquile waterfront home, Colonial Beach

Colonial Beach VA

Located in Colonial Beach, this vacation home is on the waterfront, within a 15-minute drive of Ingleside Vineyards and Monrovia.

Shewell's A-Frame on Mill Creek

Lusby MD

With a stay at this vacation home in Lusby, you'll be within a 5-minute drive of Chesapeake Bay and Drum Point Lake.

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.

Discover tranquility near Calvert Cliffs

Saint Leonard MD

Located in St. Leonard, this vacation home is on the waterfront, within a 10-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and Museum.

Waterfront Retreat, Private Pier, Remodeled, Epic Views, Sunsets on the River

Lexington Park MD

$399 nightly

$402 total

Jun 22 - Jun 23

Total with taxes and fees

With a stay at this vacation home in Lexington Park, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Historic St. Mary's City.

Private Pier, Main+Guest House | Luxe Waterfront Home | Bay Estate by AvantStay

Dameron MD

When you stay at this vacation home in Dameron, you'll be on the beach, just steps from Chesapeake Bay and 8 minutes by foot from Saint Jerome Beach.

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Cobb Island MD

When you stay at this vacation home in Cobb Island, you'll be on the waterfront and steps from Potomac River.

All Year Retreat - Indoor Heated Pool, Beach, Game & Movie Cottage, Sleeps 21

Hague VA

Located in Hague, this vacation home is on the waterfront, within a 15-minute drive of Coles Point Marina and Hague Winery.

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Scotland MD

$570 nightly

$629 total

Jul 6 - Jul 7

Total with taxes and fees

With a stay at this vacation home in Scotland (Point Lookout), you'll be a 1-minute drive from Chesapeake Bay and 11 minutes from Confederate Memorial Park.

FAMILY FRIENDLY CREEKSIDE GETAWAY - HIDEAWAY AND ENJOY THE FAMILY MOMENTS

Ridge MD

With a stay at this vacation home in Ridge (Point Lookout), you'll be within a 10-minute drive of Chesapeake Bay and Cardinal Gibbons Park.

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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.