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

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Leonardtown vacation homes

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 AED 977
AED 2,226 total
includes taxes & fees
3 Aug - 4 Aug
Riverfront Home w/Dock · Fire Pit · Kids Play Area
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, (1 review)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 413
AED 913 total
includes taxes & fees
14 Jul - 15 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Interior

Waterfront with spectacular view, close to restaurants and bars

Waterfront with spectacular view, close to restaurants and bars
Colonial Beach
9.8 out of 10, Exceptional, (73 reviews)
"We had a wonderful stay in this clean, beautiful waterfront property. The location was fantastic, and we loved watching the swan and osprey go about their days from the front porch. We were two couples (ages 45-75!), and the place and town were the perfect, relaxing getaway. "
United States
Alexis V.
The price is AED 397
AED 1,137 total
includes taxes & fees
17 Jul - 18 Jul
Waterfront with spectacular view, close to restaurants and bars
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 AED 764
AED 2,302 total
includes taxes & fees
14 Jul - 15 Jul
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
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 AED 1,412
AED 2,626 total
includes taxes & fees
8 Aug - 9 Aug
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
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, (10 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 AED 779
AED 1,565 total
includes taxes & fees
10 Aug - 11 Aug
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 AED 826
AED 1,382 total
includes taxes & fees
12 Jul - 13 Jul
Bright and airy waterfront getaway
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, (22 reviews)
"A tranquil space with many activity options available right on site"
United States
Alyson L.
The price is AED 918
AED 1,986 total
includes taxes & fees
12 Jul - 13 Jul
River Refresh - Waterfront with Spa on Placid Bay
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 AED 1,260
AED 2,631 total
includes taxes & fees
13 Jul - 14 Jul
Charming Waterfront 3-bedroom house in Piney Point
Smart TV, fireplace, table tennis, 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, (134 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.
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!
Outdoor dining

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (37 reviews)
"Great spot"
United States
SHAWN W.
The price is AED 1,467
AED 2,647 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront Reset: Views, Games, Boats & Total Calm
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 AED 1,469
AED 2,958 total
includes taxes & fees
12 Jul - 13 Jul
4-BR Waterfront Turret Home
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 AED 1,697
AED 3,146 total
includes taxes & fees
22 Jul - 23 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Exterior

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
'The Bayside Escape' Remote Chesapeake Bay Estate
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 AED 1,910
AED 4,678 total
includes taxes & fees
21 Jul - 22 Jul
Lakefront Cabin Near Solomons Island w/ Hot Tub
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

Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

10/10 Excellent
"Outstanding hotel experience. Great staff. Great room. Great breakfast."
Bonnie 1-night trip
Posted 9 hours ago
Springhill Suites by Marriott Prince Frederick

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