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

Leonardtown Holiday Rentals

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Our top choices for Leonardtown holiday 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 NZ$982
includes taxes & fees
28 Sept - 29 Sept
Anne & Fred`s Leonardtown Home W/ Arcade room!

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is NZ$423
includes taxes & fees
5 Oct - 6 Oct
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, (61 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is NZ$533
includes taxes & fees
30 Sept - 1 Oct
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, (55 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 NZ$579
includes taxes & fees
21 Sept - 22 Sept
Cozy Virginia Potomac Riverfront Cottage

5. 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 NZ$548
includes taxes & fees
23 Sept - 24 Sept
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

6. 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 NZ$822
includes taxes & fees
29 Sept - 30 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is NZ$452
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

8. 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 NZ$465
includes taxes & fees
19 Sept - 20 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9. 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 NZ$440
includes taxes & fees
14 Oct - 15 Oct
Rest & Recharge, A-frame Cabin on Winery Grounds

10. 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, (16 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is NZ$666
includes taxes & fees
30 Sept - 1 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

11. 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 NZ$502
includes taxes & fees
23 Sept - 24 Sept
Sail Away

12. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 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 NZ$641
includes taxes & fees
19 Sept - 20 Sept
Bright and airy waterfront getaway

13. Waterfront Game-Themed Getaway · Dock & Kayaks

Waterfront Game-Themed Getaway · Dock & Kayaks
Montross
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
The price is NZ$886
includes taxes & fees
28 Sept - 29 Sept
Waterfront Game-Themed Getaway · Dock & Kayaks

14. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,217
includes taxes & fees
21 Sept - 22 Sept
4-BR Waterfront Turret Home

15. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is NZ$740
includes taxes & fees
28 Sept - 29 Sept
2 Bedroom Cottage at Coles Point Marina

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, (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 NZ$1,266
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point

17. 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 NZ$502
includes taxes & fees
23 Sept - 24 Sept
Sail Away To

18. 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 NZ$911
includes taxes & fees
18 Oct - 19 Oct
River Refresh - Waterfront with Spa on Placid Bay

19. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,721
includes taxes & fees
29 Sept - 30 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Leonardtown holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Leonardtown. 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 Leonardtown. 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 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 holiday 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 Leonardtown short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals in Leonardtown close to St. Mary's County Arts Council, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Leonardtown has to offer?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: This holiday home rental outside of Leonardtown offers a fireplace, a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Leonardtown?

With 9 Expedia holiday rentals, you're guaranteed 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 scenic spots to enjoy the outdoors, whereas North End Gallery is one of the cultural attractions. While here, Leonardtown Town Hall and Breton Bay Golf Course are other places worth a visit.

What’s a holiday rental in Leonardtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leonardtown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.