A rural landscape with a barn, trees, and a fence under a sunset sky.

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Check prices for these dates

In two weeks
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Leonardtown cottages

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (54 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is AU$451
includes taxes & fees
22 July - 23 July
Soul Oasis - home on the Chesapeake Bay
Property grounds

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
9.2 out of 10, Wonderful, (10 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is AU$384
includes taxes & fees
15 July - 16 July
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"Second time here and we love the convenience to Prince Frederick and the comfort offered by the hosts. "
United States
RACHEL S.
The price is AU$514
includes taxes & fees
3 July - 4 July
Cottage Located on the Patuxent River!
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AU$603
includes taxes & fees
6 July - 7 July
2 Bedroom Cottage at Coles Point Marina
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is AU$1,321
includes taxes & fees
5 July - 6 July
'the Bayside Escape' Remote Chesapeake Bay Estate
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is AU$1,655
includes taxes & fees
6 July - 7 July
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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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Top Leonardtown Hotel Reviews

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"A good over night accommodation. Staff was very helpful and friendly. Plenty of eating places near by. A good place to stay if your touring Southern Maryland."
Gregory 1-night trip
Posted 5 hours ago
avid hotel California - Lexington Park by IHG

Find out more about Leonardtown

Leonardtown Cottages information

Number of reviews
107
Accommodation
124 Cottages
Lowest Price
AU$384
Highest Price
AU$1,655

Frequently asked questions

What is there to do in Leonardtown near my cottage?
You'll find plenty of fun things to do in Leonardtown. Discover popular attractions like St. Marys River State Park, Port of Leonardtown Winery and St. Clements Island State Park. New Towne Neck State Park, Greenwell State Park and Sotterley Plantation are also on many to-do lists.