Early morning fog over Breton Bay, Leonardtown, Maryland, December 2018.

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 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, (50 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is €279
includes taxes & fees
17 Jun - 18 Jun
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, (9 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 €231
includes taxes & fees
16 Jun - 17 Jun
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (14 reviews)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
The price is €359
includes taxes & fees
15 Jul - 16 Jul
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is €316
includes taxes & fees
16 Jun - 17 Jun
Cottage Located on the Patuxent River!
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
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 €804
includes taxes & fees
5 Jul - 6 Jul
'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 €953
includes taxes & fees
16 Jun - 17 Jun
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

Holiday Inn Express Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

6/10 Okay
"Whenever you bring kids to a proper type setting just make sure they are well mannered and respectful"
Joseph 1-night trip
Posted 2 hours ago
Holiday Inn Express Prince Frederick by IHG

Find out more about Leonardtown

Leonardtown Cottages information

Number of reviews
116
Accommodation
123 Cottages
Lowest Price
€231
Highest Price
€953

Frequently asked questions

Why book your cottage in Leonardtown with Expedia?
Expedia has some terrific cottages in Leonardtown, so get ready for a memorable holiday on nature's doorstep. If you have a budget in mind, click on how much you want to spend and the preferred star rating of your property. Or take advantage of our filters to search for cottages with free WiFi or a pool. We'll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Leonardtown?
A good way to locate cheap cottages in Leonardtown is with Expedia's filter tool. Tailor your search results by star rating, amenities and budget to discover awesome rates in a few clicks.
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.