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Search results; 725 homes in Leonardtown

Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds, 1 private bathroom
12–17 Jul
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4.96 out of 5 average rating, 260 reviews
Guest favourite
Room in Leonardtown
Air BnB available for single professional.
4.97 out of 5 average rating, 185 reviews, 1 king bed, 1 bathroom
12–17 Jul
Top guest favourite
Home in Leonardtown
Potomac Fishing & Crab Paradise at Toney's Landing
4.94 out of 5 average rating, 32 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Top guest favourite
Flat in Leonardtown
Retreat at Fenwick
4.95 out of 5 average rating, 110 reviews, 1 bedroom, 4 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Leonardtown
The Downtown Leonardtown Hideaway!
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Jul
Guest favourite
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
4.96 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
4.99 out of 5 average rating, 132 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Oct
Top guest favourite
Townhouse in Leonardtown
Charming Duplex in the heart of Leonardtown
4.99 out of 5 average rating, 120 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
28 Jul – 2 Aug
Superhost
Home in Leonardtown
Anne & Fred's Leonardtown Home W/ Arcade room!
4.88 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
Superhost
Home in Leonardtown
Hidden Harbor House
4.82 out of 5 average rating, 11 reviews, 3 bedrooms, 3 beds, 1 bathroom
8–13 Jul
Guest favourite
Home in Leonardtown
Abells Wharf Cottage - Natural Splendor Getaway
4.93 out of 5 average rating, 45 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Jul
Top guest favourite
Home in Leonardtown
The River House: A private waterfront oasis…
4.96 out of 5 average rating, 89 reviews, 3 bedrooms, 4 beds, 3 bathrooms
13–18 Aug
Home in Leonardtown
Leonardtown waterfront paradise / Saint Clements
4.8 out of 5 average rating, 15 reviews, 3 bedrooms, 4 beds, 2 bathrooms
8–13 Jul
Home in Montross
The Rivah House
New place to stay, 4 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Cabin in Mechanicsville
Cozy Country Cabin
4.99 out of 5 average rating, 96 reviews, 2 bedrooms, 3 beds, 1 bathroom
13–18 Jul
Top guest favourite
Cottage in Cobb Island
*Waterfront Island Hideaway-A true hidden Gem*
4.97 out of 5 average rating, 93 reviews, 2 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
4.97 out of 5 average rating, 128 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
Superhost
Home in Mechanicsville
St. Mary's County Home with a View
4.62 out of 5 average rating, 209 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
17–22 Jul
Guest favourite
Home in Leonardtown
In Leonardtown Square! Walk to wharf, shops, food!
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 6 beds, 1.5 bathrooms
12–17 Jul