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

Holiday Homes in Leonardtown

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Leonardtown holiday homes

A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

1. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful location "
United States
Jonathan M.
The price is €748
includes taxes & fees
26 Oct - 27 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!
A coastal area with a sandy beach, a small settlement, and a clear view of the sea.

2. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is €437
includes taxes & fees
8 Oct - 9 Oct
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

3. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €233
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A covered patio with a view of a lake, furnished with chairs and a table.

4. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is €341
includes taxes & fees
5 Oct - 6 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

5. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.6 out of 10, Exceptional, (14 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is €285
includes taxes & fees
13 Oct - 14 Oct
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

6. Waterfront Game-Themed Getaway · Dock & Kayaks

Waterfront Game-Themed Getaway · Dock & Kayaks
Montross
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is €435
includes taxes & fees
28 Oct - 29 Oct
Waterfront Game-Themed Getaway · Dock & Kayaks
A spacious living room with a large sofa, a television, and a view of the ocean.

7. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €644
includes taxes & fees
28 Sept - 29 Sept
4-BR Waterfront Turret Home
A lakeside view with chairs and a table, a rainbow, and trees.

8. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is €314
includes taxes & fees
28 Sept - 29 Sept
Bright and airy waterfront getaway
A two-story house with a balcony, surrounded by trees and a wooden fence.

9. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (7 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is €650
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

10. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €864
includes taxes & fees
29 Sept - 30 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A pathway lined with trees and lights leading to a wooden building with a visible window.

11. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is €753
includes taxes & fees
28 Sept - 29 Sept
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is €1,053
includes taxes & fees
28 Sept - 29 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub
A deck with outdoor furniture overlooking a lake.

13. River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (25 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is €464
includes taxes & fees
1 Oct - 2 Oct
River Refresh - Waterfront with Spa on Placid Bay
A covered outdoor deck with wicker furniture, a glass door leading inside, and a view of a lake surrounded by trees.

14. Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Heathsville
9.6 out of 10, Exceptional, (35 reviews)
"We loved the tranquility of the place, beautiful views, and the unique design of the house. The host was very responsive. It was a very relaxing stay. I am sure we will be coming back soon."
United States
Liudmila U.
The price is €553
includes taxes & fees
28 Sept - 29 Sept
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
A lakeside property with a large house, a shed, and a dense forest in the background.

15. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
'The Bayside Escape' Remote Chesapeake Bay Estate
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

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

8/10 Good
"The environment was welcoming. The facility was well-kept. The breakfast buffet delicious and warm. The staff was professional and responsive to our requests. The 1 noteworthy drawback was the 150.00 deposit required at registration."
Dorothy 2-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Find out more about Leonardtown

Leonardtown Holiday Homes information

Number of reviews
212
Accommodation
276 Holiday Homes
Lowest Price
€233
Highest Price
€1,053