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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Leonardtown holiday homes

TV, fireplace

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, (3 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$423
includes taxes & fees
24 Aug - 25 Aug
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Interior

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, (11 reviews)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is AU$537
includes taxes & fees
27 July - 28 July
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is AU$538
includes taxes & fees
4 Aug - 5 Aug
Bright and airy waterfront getaway
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is AU$1,193
includes taxes & fees
4 Aug - 5 Aug
4-BR Waterfront Turret Home
Property grounds

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
9.4 out of 10, Exceptional, (13 reviews)
"This place is fantastic!!Great responsive owners! Fantastic location, perfectly stocked kitchen, comfy beds and bar none the cleanest place I’ve stayed!! The house is adorable and comfortable with a rocking fire pit. The location is walkable and yet quiet!Stay here!No notes!!"
United States
Amanda M.
The price is AU$664
includes taxes & fees
12 Aug - 13 Aug
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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$1,120
includes taxes & fees
4 Aug - 5 Aug
Charming Waterfront 3-bedroom house in Piney Point
Outdoor dining

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (38 reviews)
"The host went above and beyond to make us feel welcome. From the smooth check-in to the thoughtful welcome basket, every detail was handled with care. We especially loved the riverfront home and all the commodities included. A true home away from home!"
United States
Evelyn C.
The price is AU$1,110
includes taxes & fees
27 July - 28 July
Waterfront Reset: Views, Games, Boats & Total Calm
Exterior

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is AU$768
includes taxes & fees
4 Aug - 5 Aug
River Refresh - Waterfront with Spa on Placid Bay
Interior

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$1,615
includes taxes & fees
27 July - 28 July
Lakefront Cabin Near Solomons Island w/ Hot Tub
Property grounds

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, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is AU$1,206
includes taxes & fees
26 July - 27 July
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Terrace/patio

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, (34 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$953
includes taxes & fees
27 July - 28 July
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Coffee/tea maker, fridge, microwave, oven

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, (16 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$1,068
includes taxes & fees
4 Aug - 5 Aug
Riverfront Home w/Dock · Fire Pit · Kids Play Area
TV, fireplace, video games, books

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 AU$1,432
includes taxes & fees
12 Aug - 13 Aug
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Smart TV, fireplace, ping pong, books

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Point Lookout
10.0 out of 10, Exceptional, (135 reviews)
"The property was very clean and well-stocked. Beds were comfortable and pictures matched reality. Jocelyn was so kind to leave us ingredients for smores and Easter eggs for my kids to have a hunt in the backyard. Overall, we had a wonderful stay and hope to make it back again some time!"
United States
Allie P.
The price is AU$932
includes taxes & fees
20 Aug - 21 Aug
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (14 reviews)
"Listing was accurate; communication with host was great and helpful. We had a wonderful family time."
United States
Melissa D.
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Exterior

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
'The Bayside Escape' Remote Chesapeake Bay Estate
Terrace/patio

Coastal Grace | Hot Tub, Game Room, & Fenced Yard

Coastal Grace | Hot Tub, Game Room, & Fenced Yard
Colonial Beach
10.0 out of 10, Exceptional, (1 review)
"Great time and the property was better than expected. Our son who had autism stayed with us and it is great for people with sensory issues. VERY quiet and we never saw a neighbor!"
United States
Amanda O.
The price is AU$907
includes taxes & fees
15 Aug - 16 Aug
Coastal Grace | Hot Tub, Game Room, & Fenced Yard
Dining

Charming 6BR Colonial Beach Retreat, Walk to the Beach

Charming 6BR Colonial Beach Retreat, Walk to the Beach
Colonial Beach
The price is AU$1,396
includes taxes & fees
29 July - 30 July
Charming 6BR Colonial Beach Retreat, Walk to the Beach
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

Spark by Hilton California Lexington Park

Spark by Hilton California Lexington Park

10/10 Excellent
"Place was awesome and the staff was extremely friendly and helpful."
Vincent 2-night trip
Posted 23 hours ago
Spark by Hilton California Lexington Park

Find out more about Leonardtown

Leonardtown Holiday Homes information

Number of reviews
318
Accommodation
277 Holiday Homes
Lowest Price
AU$423
Highest Price
AU$1,615