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

Leonardtown Vacation Rentals

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Our top choices for Leonardtown vacation rentals

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 CA $327
CA $810 total
includes taxes & fees
Aug 16 - Aug 17
Anne & Fred`s Leonardtown Home W/ Arcade room!

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $269
CA $421 total
includes taxes & fees
Aug 19 - Aug 20
Coles Point Marina

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is CA $217
CA $444 total
includes taxes & fees
Sep 8 - Sep 9
Soul Oasis - home on the Chesapeake Bay

4. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (51 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 CA $244
CA $474 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Virginia Potomac Riverfront Cottage

5. 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
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
The price is CA $213
CA $372 total
includes taxes & fees
Aug 25 - Aug 26
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (70 reviews)
"Always a great stay! "
United States
Amy H.
The price is CA $158
CA $364 total
includes taxes & fees
Aug 18 - Aug 19
Rest & Recharge, A-frame Cabin on Winery Grounds

7. 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, (5 reviews)
The price is CA $188
CA $385 total
includes taxes & fees
Aug 18 - Aug 19
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

8. 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 CA $122
CA $466 total
includes taxes & fees
Sep 8 - Sep 9
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

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, (12 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $297
CA $593 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

10. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $480
CA $595 total
includes taxes & fees
Aug 13 - Aug 14
2 Bedroom Cottage at Coles Point Marina

11. 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 CA $418
CA $1,009 total
includes taxes & fees
Sep 8 - Sep 9
4-BR Waterfront Turret Home

12. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (21 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 CA $305
CA $516 total
includes taxes & fees
Aug 25 - Aug 26
Bright and airy waterfront getaway

13. 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 CA $209
CA $459 total
includes taxes & fees
Aug 31 - Sep 1
Sail Away

14. 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 CA $241
CA $521 total
includes taxes & fees
Aug 19 - Aug 20
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

15. Waterfront Reset: Views, Games, Boats & Total Calm

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (38 reviews)
"What a lovely weekend. Beautiful views, winery at Ingleside , breakfast and shopping in Warsaw, grilling and paddle boating. Thank you. It was just what we needed!!’"
United States
Diana H.
The price is CA $474
CA $893 total
includes taxes & fees
Sep 1 - Sep 2
Waterfront Reset: Views, Games, Boats & Total Calm

16. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (5 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 CA $477
CA $1,095 total
includes taxes & fees
Aug 18 - Aug 19
Charming Waterfront 3-bedroom house in Piney Point

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, (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 CA $348
CA $819 total
includes taxes & fees
Sep 1 - Sep 2
Riverfront Home w/Dock · Fire Pit · Kids Play Area

18. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is CA $603
CA $1,621 total
includes taxes & fees
Aug 13 - Aug 14
Lakefront Cabin Near Solomons Island w/ Hot Tub

19. River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful, clean, comfortable home in an idyllic location. "
United States
Kelly P.
The price is CA $341
CA $741 total
includes taxes & fees
Aug 23 - Aug 24
River Refresh - Waterfront with Spa on Placid Bay

20. 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 CA $643
CA $1,201 total
includes taxes & fees
Aug 16 - Aug 17
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
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

Find out more about Leonardtown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Leonardtown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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 10 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 Leonardtown Library 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.