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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is AU$1,167
includes taxes & fees
2 Nov - 3 Nov
2 Acre Oasis with Private Beach! Family and dog friendly!
A spacious living room with a large sofa, a television, and a view of the ocean.

2. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$1,056
includes taxes & fees
3 Nov - 4 Nov
4-BR Waterfront Turret Home
A modern kitchen with stainless steel appliances, a central island, and a dining area with a view of the outdoors.

3. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AU$677
includes taxes & fees
1 Nov - 2 Nov
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

4. 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, (16 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is AU$463
includes taxes & fees
1 Nov - 2 Nov
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A covered patio with a view of a lake, furnished with chairs and a table.

5. 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, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AU$553
includes taxes & fees
29 Nov - 30 Nov
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

6. 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 AU$400
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

7. 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, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is AU$1,371
includes taxes & fees
3 Nov - 4 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

8. Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (40 reviews)
"We really enjoyed our stay at this lake house. The view is beautiful and the house is beautifully decorated and kid friendly. Just a really charming place to stay for a family vacation."
United States
Nicole P.
The price is AU$664
includes taxes & fees
2 Nov - 3 Nov
Waterfront Reset: Views, Games, Boats & Total Calm
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 AU$1,050
includes taxes & fees
4 Nov - 5 Nov
Charming Waterfront 3-bedroom house in Piney Point
A pathway lined with trees and lights leading to a wooden building with a visible window.

10. 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, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is AU$1,173
includes taxes & fees
29 Nov - 30 Nov
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.

11. 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 AU$1,590
includes taxes & fees
2 Nov - 3 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub
A lakeside view with chairs and a table, a rainbow, and trees.

12. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 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 AU$532
includes taxes & fees
2 Nov - 3 Nov
Bright and airy waterfront getaway
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

13. Riverfront Home w/Dock · Fire Pit · Kids Play Area

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (18 reviews)
"Everything about this stay was FANTASTIC. The host was amazing, the condo was in excellent condition and the view is AMAZING! Enjoyed everything about this stay!"
United States
N C.
The price is AU$727
includes taxes & fees
1 Nov - 2 Nov
Riverfront Home w/Dock · Fire Pit · Kids Play Area
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

14. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is AU$431
includes taxes & fees
2 Nov - 3 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A dining area with a wooden table, chairs, and a bottle of wine.

15. 1 m. to Beaches & Town, Grill, Deck, Outdoor Seating

1 m. to Beaches & Town, Grill, Deck, Outdoor Seating
Colonial Beach
10.0 out of 10, Exceptional, (7 reviews)
"This was such a lovely place with lots of room and it was close to the beach too. I plan to come back soon."
United States
Cynthia H.
The price is AU$683
includes taxes & fees
2 Nov - 3 Nov
1 m. to Beaches & Town, Grill, Deck, Outdoor Seating
A modern kitchen with a central island, bar stools, pendant lights, and a wooden cabinet.

16. The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly

The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly
Colonial Beach
10.0 out of 10, Exceptional, (18 reviews)
"Loved staying at this property. Great for a girls weekend away."
United States
Jennifer B.
The price is AU$1,335
includes taxes & fees
2 Nov - 3 Nov
The Lyellton House: 6 Bd 4Ba - Steps to Shops & Shore - Pet Friendly
A deck with outdoor furniture overlooking a lake.

17. River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (26 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is AU$754
includes taxes & fees
3 Nov - 4 Nov
River Refresh - Waterfront with Spa on Placid Bay
A small, single-story house with a red door, a porch with white railings, and a brick pathway leading to the entrance.

18. Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD

Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD
King George
8.4 out of 10, Very good, (5 reviews)
"Charming cottage with updated decor. The host was very comucative during a power outage due to storms. The kitchen was nicly stocked with snacks and drinks. The pool was nice, but the backyard was not very usable due to some leftovers from repair work taking up the grassy area."
United States
Kelley M.
The price is AU$399
includes taxes & fees
2 Nov - 3 Nov
Cozy 3 Bdrm home in King George. 5 mins to Dahlgren Naval Base and Southern MD
A covered outdoor deck with wicker furniture, a glass door leading inside, and a view of a lake surrounded by trees.

19. 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 AU$897
includes taxes & fees
4 Nov - 5 Nov
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
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
"Quiet clean, decent breakfast, plenty of parking"
Terri 1-night trip
Posted 4 hours ago
avid hotel California - Lexington Park by IHG

Find out more about Leonardtown

Leonardtown Holiday Homes information

Number of reviews
300
Accommodation
270 Holiday Homes
Lowest Price
AU$399
Highest Price
AU$1,590