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

Holiday Homes in Leonardtown

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Leonardtown holiday homes

Terrace/patio

Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
10.0 out of 10, Exceptional, (1 review)
"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."
United States
Paige
The price is €558
includes taxes & fees
6 Jul - 7 Jul
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Fridge, microwave, oven, stovetop

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, (15 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 €490
includes taxes & fees
29 Jun - 30 Jun
Riverfront Home w/Dock · Fire Pit · Kids Play Area
TV, books, stereo

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (22 reviews)
"A tranquil space with many activity options available right on site"
United States
Alyson L.
The price is €448
includes taxes & fees
16 Jul - 17 Jul
River Refresh - Waterfront with Spa on Placid 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, (33 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 €575
includes taxes & fees
18 Jun - 19 Jun
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
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, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is €344
includes taxes & fees
22 Jun - 23 Jun
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 €326
includes taxes & fees
24 Jun - 25 Jun
Bright and airy waterfront getaway
Smart TV, fireplace, ping pong, books

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (130 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is €548
includes taxes & fees
6 Jul - 7 Jul
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Smart TV

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.4 out of 10, Exceptional, (13 reviews)
"This house is great and has everything we needed. It was very clean and within walking distance of the beach and restaurants. Loved it and would book again!"
United States
Sandra S.
The price is €400
includes taxes & fees
24 Jun - 25 Jun
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
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 €554
includes taxes & fees
21 Jun - 22 Jun
Charming Waterfront 3-bedroom house in Piney Point
Outdoor dining

Waterfront Reset: Games, Views, Boats & Total Calm

Waterfront Reset: Games, Views, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (35 reviews)
"Great spot"
United States
SHAWN W.
The price is €674
includes taxes & fees
8 Jul - 9 Jul
Waterfront Reset: Games, Views, Boats & Total Calm
Interior

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is €969
includes taxes & fees
22 Jun - 23 Jun
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, (12 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 €741
includes taxes & fees
18 Jun - 19 Jun
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
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, (1 review)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €872
includes taxes & fees
30 Jun - 1 Jul
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Property grounds

Secluded Woodland Waterfront Retreat

Secluded Woodland Waterfront Retreat
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"The host was very communicative, the house was very clean and comfortable, and the river views were beautiful!"
United States
Meghan H.
The price is €497
includes taxes & fees
30 Jun - 1 Jul
Secluded Woodland Waterfront Retreat
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 €839
includes taxes & fees
22 Jun - 23 Jun
4-BR Waterfront Turret Home
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, (12 reviews)
"Clean and easy "
United States
Robert R.
The price is €539
includes taxes & fees
5 Jul - 6 Jul
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
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

Quality Inn Solomons - Beacon Marina

Quality Inn Solomons - Beacon Marina

10/10 Excellent
"location"
LORRIE JONES 1-night trip
Posted 8 hours ago
Quality Inn Solomons - Beacon Marina

Find out more about Leonardtown

Leonardtown Holiday Homes information

Number of reviews
308
Accommodation
254 Holiday Homes
Lowest Price
€326
Highest Price
€969