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Find holiday rentals that suit your style

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Cabins
Cabins
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Cottages
Cottages

Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Leonardtown cottages

A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

1. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is NZ$526
includes taxes & fees
17 Nov - 18 Nov
Soul Oasis - home on the Chesapeake Bay
A house with a gravel driveway leading to a dock by the water.

2. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (57 reviews)
"My family and I had a great time at this property fishing and crabbing. We also did a day trip to Westmoreland State Park, where we got to hike to Fossils Beach."
United States
Carmelita A.
The price is NZ$573
includes taxes & fees
14 Nov - 15 Nov
Cozy Virginia Potomac Riverfront Cottage
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

3. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is NZ$473
includes taxes & fees
13 Nov - 14 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A single-story house with a front porch, a small deck, and a number '4' on the side.

4. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is NZ$708
includes taxes & fees
13 Nov - 14 Nov
2 Bedroom Cottage at Coles Point Marina
A single-story house with a porch, a wooden fence with a neon sign, and a welcome flag.

5. The Sugar Shack - charming, fully renovated 1930s cottage with AC

The Sugar Shack - charming, fully renovated 1930s cottage with AC
Colonial Beach
The price is NZ$571
includes taxes & fees
7 Dec - 8 Dec
The Sugar Shack - charming, fully renovated 1930s cottage with AC
A red house with a porch decorated with pumpkins and flowers.

6. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is NZ$2,041
includes taxes & fees
22 Nov - 23 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub
A single-story house with a front porch, a small deck, and a wooden walkway leading to the door.

7. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.0 out of 10, Wonderful, (22 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is NZ$738
includes taxes & fees
1 Dec - 2 Dec
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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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Learn more about Leonardtown

Explore the historic waterfront square where local artisans showcase their crafts and restaurants serve fresh Chesapeake Bay seafood. Kayak along Breton Bay's peaceful waters or visit the nearby Patuxent River Naval Air Museum in Lexington Park.

See all hotels in Leonardtown
A rural landscape with a barn, trees, and a fence under a sunset sky.

Frequently Asked Questions

What is there to do in Leonardtown near my cottage?

The most useful travel accessory is a well-planned itinerary. Port of Leonardtown Winery is an excellent place to kick off your sightseeing in Leonardtown.