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

Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Leonardtown vacation rentals

A modern kitchen with dark cabinets, a dishwasher, and a countertop with a sink.

1. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is AED 878
AED 2,133 total
includes taxes & fees
18 Oct - 19 Oct
Anne & Fred`s Leonardtown Home W/ Arcade room!
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

2. 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 AED 1,455
AED 3,109 total
includes taxes & fees
26 Oct - 27 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!
A single-story house with a front porch, a small deck, and a number '4' on the side.

3. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AED 507
AED 891 total
includes taxes & fees
19 Oct - 20 Oct
Coles Point Marina
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 AED 289
AED 1,193 total
includes taxes & fees
28 Oct - 29 Oct
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

5. 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 AED 476
AED 995 total
includes taxes & fees
26 Oct - 27 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A bedroom with a bed, a bench, a nightstand, a ceiling fan, and large windows.

6. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AED 662
AED 1,767 total
includes taxes & fees
18 Oct - 19 Oct
Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK
A wooden cabin with a balcony, surrounded by lush greenery and trees.

7. Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (73 reviews)
"Always a great stay! "
United States
Amy H.
The price is AED 430
AED 983 total
includes taxes & fees
9 Nov - 10 Nov
Rest & Recharge, A-frame Cabin on Winery Grounds
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

8. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (56 reviews)
"This is our 4th time to come here and the view still amaze me. Fishing is great in this area. My family and I really had an amazing, fun and relaxing stay as always. See you next time."
United States
Natt L.
The price is AED 643
AED 1,251 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Virginia Potomac Riverfront Cottage
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

9. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is AED 562
AED 977 total
includes taxes & fees
18 Oct - 19 Oct
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Private kitchen

10. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
The price is AED 579
AED 841 total
includes taxes & fees
21 Oct - 22 Oct
Just a getaway piece of property
A spacious living room with a large sofa, a television, and a view of the ocean.

11. 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 AED 1,102
AED 2,697 total
includes taxes & fees
18 Oct - 19 Oct
4-BR Waterfront Turret Home
A covered patio with a view of a lake, furnished with chairs and a table.

12. 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 AED 735
AED 1,501 total
includes taxes & fees
20 Oct - 21 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

13. 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, (3 reviews)
"We loved the quiet location, the privacy, and the dock out back. The house was stocked with everything we needed!"
United States
Nicholas L.
The price is AED 1,293
AED 3,550 total
includes taxes & fees
20 Oct - 21 Oct
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.

14. 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 AED 874
AED 1,819 total
includes taxes & fees
17 Nov - 18 Nov
Waterfront Reset: Views, Games, Boats & Total Calm
A balcony with a white railing, outdoor furniture, and a view of the sea.

15. Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (13 reviews)
"we liked everything and location!!!"
United States
Shawn
The price is AED 444
AED 1,083 total
includes taxes & fees
20 Oct - 21 Oct
Sail Away
A lakeside view with chairs and a table, a rainbow, and trees.

16. 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 AED 760
AED 1,304 total
includes taxes & fees
18 Oct - 19 Oct
Bright and airy waterfront getaway
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

17. 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 AED 771
AED 1,974 total
includes taxes & fees
18 Oct - 19 Oct
Riverfront Home w/Dock · Fire Pit · Kids Play Area
A two-story house with a balcony, surrounded by trees and a wooden fence.

18. 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 AED 1,131
AED 2,743 total
includes taxes & fees
30 Oct - 31 Oct
Charming Waterfront 3-bedroom house in Piney Point
A single-story house with a front porch, a small deck, and a number '4' on the side.

19. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AED 1,267
AED 1,567 total
includes taxes & fees
18 Oct - 19 Oct
2 Bedroom Cottage at Coles Point Marina
A wooden gazebo with benches, a yellow-painted floor, and a view of the ocean.

20. 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 AED 721
AED 1,784 total
includes taxes & fees
18 Oct - 19 Oct
1 m. to Beaches & Town, Grill, Deck, Outdoor Seating
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

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick

10/10 Excellent
"The check in process was smooth and the front desk person was nice and helpful. The room was actually nice and clean. Shower pressure was perfect. The bed was really firm. I’m not a fan of extremely firm beds."
LaPrince 1-night trip
Posted 5 hours ago
SureStay by Best Western Prince Frederick

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals in Leonardtown near St. Mary's County Arts Council, or you can choose a more secluded option if you're looking for extra privacy while you relax. Leonardtown is known for its seafood restaurants and festivals. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best vacation rentals that Leonardtown has to offer?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This vacation home rental near Leonardtown offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Leonardtown?

With 9 Expedia vacation rentals, you're sure to find just the right place for your Leonardtown stay.

What’s there to see and do in Leonardtown?

St. Mary's River State Park and Indian Village Archeological Park are a couple of scenic spots to enjoy the outdoors, whereas North End Gallery is one of the cultural attractions. While here, Breton Bay Golf Course and Leonardtown Town Hall are other places worth a visit.

What’s a vacation rental in Leonardtown like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Leonardtown. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip.