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

Search Vacation Homes in Leonardtown

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Leonardtown vacation homes

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 1,120 total
includes taxes & fees
17 Jul - 18 Jul
Waterfront with spectacular view, close to restaurants and bars

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 426
AED 927 total
includes taxes & fees
13 Jul - 14 Jul
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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 845
AED 1,417 total
includes taxes & fees
8 Jul - 9 Jul
Bright and airy waterfront getaway

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 749
AED 1,516 total
includes taxes & fees
27 Jul - 28 Jul
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

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 1,970 total
includes taxes & fees
12 Jul - 13 Jul
River Refresh - Waterfront with Spa on Placid Bay

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 property is wonderful and the host was very responsive on some minor issues. The place is decorated so nicely and I really appreciated that all of the cookware, utensils and appliances were clean and new! The fenced in back yard is a huge plus for those with pets and children. Would definitely stay again!"
United States
Sharon V.
The price is AED 698
AED 1,697 total
includes taxes & fees
19 Jul - 20 Jul
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

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 945
AED 2,518 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

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 2,376 total
includes taxes & fees
13 Jul - 14 Jul
Charming Waterfront 3-bedroom house in Piney Point

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, (133 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 AED 1,286
AED 2,432 total
includes taxes & fees
19 Jul - 20 Jul
Hideaway in Hays Beach: Western Sandy Shore of Chesapeake Bay and 5g WiFi!

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 3,087 total
includes taxes & fees
6 Jul - 7 Jul
4-BR Waterfront Turret Home

Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (36 reviews)
"Great spot"
United States
SHAWN W.
The price is AED 1,687
AED 2,919 total
includes taxes & fees
28 Jul - 29 Jul
Waterfront Reset: Views, Games, Boats & Total Calm

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 AED 1,697
AED 3,154 total
includes taxes & fees
6 Jul - 7 Jul
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

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 1,991
AED 4,620 total
includes taxes & fees
6 Jul - 7 Jul
Lakefront Cabin near Solomons Island w/ Hot Tub

'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
The price is AED 1,407
AED 3,403 total
includes taxes & fees
29 Jul - 30 Jul
'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.
Save an average of 15% on thousands of hotels when you're signed in

Top Leonardtown Hotel Reviews

Explore a world of travel with Expedia