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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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 ￥38,254
￥94,324 total
includes taxes & fees
Sep 1 - Sep 2
Anne & Fred`s Leonardtown Home W/ Arcade room!
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

2. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is ￥24,974
￥51,587 total
includes taxes & fees
Sep 29 - Sep 30
Soul Oasis - home on the Chesapeake Bay
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

3. 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, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥19,451
￥42,000 total
includes taxes & fees
Sep 2 - Sep 3
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
An aerial view of a coastal area with a sandy beach, a small settlement with houses, and a calm sea.

4. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr 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 ￥26,642
￥76,015 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

5. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (54 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is ￥28,016
￥54,868 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Virginia Potomac Riverfront Cottage
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

6. 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)
"The owner was very nice "
United States
karen
The price is ￥24,494
￥43,111 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
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, (71 reviews)
"Always a great stay! "
United States
Amy H.
The price is ￥15,849
￥39,363 total
includes taxes & fees
Sep 1 - Sep 2
Rest & Recharge, A-frame Cabin on Winery Grounds
A single-story house with a front porch, a small deck, and a number '4' on the side.

8. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥30,911
￥48,436 total
includes taxes & fees
Sep 1 - Sep 2
Coles Point Marina
A covered patio with a view of a lake, furnished with chairs and a table.

9. 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, (15 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is ￥28,016
￥61,776 total
includes taxes & fees
Sep 8 - Sep 9
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

10. 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)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is ￥14,178
￥54,266 total
includes taxes & fees
Sep 8 - Sep 9
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A lakeside view with chairs and a table, a rainbow, and trees.

11. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 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 ￥33,139
￥57,697 total
includes taxes & fees
Sep 1 - Sep 2
Bright and airy waterfront getaway
A waterfront hotel with a long pier extending into the water, a large building with multiple floors, and a clear sky.

12. Sail Away To

Sail Away To
Colonial Beach
9.6 out of 10, Exceptional, (17 reviews)
"The apartment was beautiful. he location made it easy to get around. Being able up front to the bay was awesome. Had my morning coffee on the deck."
United States
Christina
The price is ￥18,891
￥46,206 total
includes taxes & fees
Sep 22 - Sep 23
Sail Away To
A room with a wooden bench, a small table, and a view of the outdoors.

13. 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 ￥42,424
￥80,645 total
includes taxes & fees
Sep 28 - Sep 29
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
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, (39 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is ￥35,795
￥80,399 total
includes taxes & fees
Sep 29 - Sep 30
Waterfront Reset: Views, Games, Boats & Total Calm

15. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Lusby
The price is ￥31,410
￥66,724 total
includes taxes & fees
Sep 2 - Sep 3
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
A spacious living room with a large sofa, a television, and a view of the ocean.

16. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is ￥48,027
￥112,529 total
includes taxes & fees
Sep 8 - Sep 9
4-BR Waterfront Turret Home
A single-story house with a front porch, a small deck, and a number '4' on the side.

17. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is ￥55,231
￥68,629 total
includes taxes & fees
Sep 1 - Sep 2
2 Bedroom Cottage at Coles Point Marina
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 ￥54,911
￥127,757 total
includes taxes & fees
Sep 1 - Sep 2
Charming Waterfront 3-bedroom house in Piney Point
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

19. 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 ￥37,141
￥90,925 total
includes taxes & fees
Sep 10 - Sep 11
Riverfront Home w/Dock · Fire Pit · Kids Play Area
A spacious room with a high ceiling, large windows, a ceiling fan, a dining area with a table and chairs, and a sofa.

20. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy and comfortable."
United States
sandi c.
The price is ￥35,860
￥70,502 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

8/10 Good
"It was a nice clean room and the breakfast was tasty."
Joseph 1-night trip
Posted 9 hours ago
Springhill Suites by Marriott Prince Frederick

Find out more about Leonardtown

Search for holiday rentals in Leonardtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Leonardtown using one of the methods below:

  • View our selection of featured holiday rentals in Leonardtown
  • Use the map to find apartments and other holiday homes in the Leonardtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Leonardtown while they last

Look no further and take a look at our great range of rental properties in Leonardtown!

Frequently asked questions

Are there vacation rentals in Leonardtown?

Yes, there are vacation rentals in Leonardtown near Saint Mary's Fairground, 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?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental near Leonardtown is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Abell's Wharf are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Breton Bay Golf Course 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.