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

Leonardtown Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Leonardtown holiday 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 AU$808
includes taxes & fees
9 Sept - 10 Sept
Anne & Fred`s Leonardtown Home W/ Arcade room!
A single-story house with a front porch, a small deck, and a number '4' on the side.

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AU$336
includes taxes & fees
5 Oct - 6 Oct
Coles Point Marina
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

3. 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 AU$466
includes taxes & fees
9 Sept - 10 Sept
Cozy Virginia Potomac Riverfront Cottage
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 AU$618
includes taxes & fees
9 Sept - 10 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

5. 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 AU$423
includes taxes & fees
7 Oct - 8 Oct
Soul Oasis - home on the Chesapeake Bay
A wooden cabin with a balcony, surrounded by lush greenery and trees.

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, (71 reviews)
"Always a great stay! "
United States
Amy H.
The price is AU$345
includes taxes & fees
9 Sept - 10 Sept
Rest & Recharge, A-frame Cabin on Winery Grounds
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

7. 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 AU$369
includes taxes & fees
9 Sept - 10 Sept
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A covered patio with a view of a lake, furnished with chairs and a table.

8. 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 AU$519
includes taxes & fees
14 Sept - 15 Sept
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A lakeside view with chairs and a table, a rainbow, and trees.

9. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (23 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 AU$489
includes taxes & fees
9 Sept - 10 Sept
Bright and airy waterfront getaway
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

10. 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, (7 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$361
includes taxes & fees
16 Sept - 17 Sept
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

11. 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 AU$425
includes taxes & fees
10 Sept - 11 Sept
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
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 AU$412
includes taxes & fees
29 Sept - 30 Sept
Sail Away To
A spacious living room with a large sofa, a television, and a view of the ocean.

13. 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 AU$1,014
includes taxes & fees
9 Sept - 10 Sept
4-BR Waterfront Turret Home
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 AU$696
includes taxes & fees
29 Sept - 30 Sept
Waterfront Reset: Views, Games, Boats & Total Calm
A single-story house with a front porch, a small deck, and a number '4' on the side.

15. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is AU$578
includes taxes & fees
10 Sept - 11 Sept
2 Bedroom Cottage at Coles Point Marina
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

16. 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, (17 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 AU$820
includes taxes & fees
9 Sept - 10 Sept
Riverfront Home w/Dock · Fire Pit · Kids Play Area

17. 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 AU$564
includes taxes & fees
6 Oct - 7 Oct
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
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 AU$1,089
includes taxes & fees
9 Sept - 10 Sept
Charming Waterfront 3-bedroom house in Piney Point
A deck with outdoor furniture overlooking a lake.

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 AU$751
includes taxes & fees
9 Sept - 10 Sept
River Refresh - Waterfront with Spa on Placid 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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"Excellent hotel"
Eileen 1-night trip
Posted less than an hour ago
avid hotel California - Lexington Park by IHG

Find out more about Leonardtown

Everything you need to know about Leonardtown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Leonardtown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Leonardtown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Leonardtown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Leonardtown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leonardtown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leonardtown holiday rentals we have selected for you start as low as AU$361 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Leonardtown rentals

At Expedia, we put the best Leonardtown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Leonardtown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Leonardtown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Leonardtown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals in Leonardtown close to Saint Mary's Fairground, 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 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 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.