Leonardtown Vacation Rentals from $266: Search Short-Term Rentals

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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!

Leonardtown

Christy C.

$548 nightly

Oct 20 - Oct 21

Total with taxes and fees

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!

Leonardtown

Carol L.

$767 nightly

Oct 26 - Oct 27

Total with taxes and fees

A single-story house with a front porch, a small deck, and a number '4' on the side.

3. Coles Point Marina

Hague

John

$255 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Colonial Beach

Crystal W.

$292 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

Saint Leonard

Nancy P.

$261 nightly

Oct 26 - Oct 27

Total with taxes and fees

A coastal area with a sandy beach, a clear blue sea, and a small settlement with houses.

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

Montross

Julie P.

$443 nightly

Oct 26 - Oct 27

Total with taxes and fees

A wooden cabin with a balcony, surrounded by lush greenery and trees.

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

Colonial Beach

Amy H.

$246 nightly

Nov 9 - Nov 10

Total with taxes and fees

A room with a large window overlooking a beach with a wooden pier and lounge chairs.

8. Cozy Virginia Potomac Riverfront Cottage

Hague

Natt L.

$315 nightly

Oct 20 - Oct 21

Total with taxes and fees

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.

Benedict

ed r.

$241 nightly

Oct 20 - Oct 21

Total with taxes and fees

10. Just a getaway piece of property

Mechanicsville

David L.

$209 nightly

Oct 23 - Oct 24

Total with taxes and fees

A spacious living room with a large sofa, a television, and a view of the ocean.

11. 4-BR Waterfront Turret Home

Solomons

Thomas S.

$665 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Lexington Park

Andrea B.

$406 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Lusby

Nicholas L.

$961 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Montross

Nicole P.

$462 nightly

Oct 26 - Oct 27

Total with taxes and fees

A balcony with a white railing, outdoor furniture, and a view of the sea.

15. Sail Away

Colonial Beach

Shawn

$288 nightly

Oct 20 - Oct 21

Total with taxes and fees

A lakeside view with chairs and a table, a rainbow, and trees.

16. Bright and airy waterfront getaway

Benedict

George

$335 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Montross

N C.

$479 nightly

Oct 20 - Oct 21

Total with taxes and fees

A two-story house with a balcony, surrounded by trees and a wooden fence.

18. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

$676 nightly

Oct 30 - Oct 31

Total with taxes and fees

19. 2 Bedroom Cottage at Coles Point Marina

Hague

$389 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Colonial Beach

Cynthia H.

$439 nightly

Oct 20 - Oct 21

Total with taxes and fees

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Top Leonardtown Hotel Reviews

Holiday Inn Express and Suites King George- Dahlgren by IHG

10/10 Excellent

"Very quiet, rooms clean and staff was great. Breakfast was very nice."

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent

"Breakfast was great with hot options like eggs,sausage and make your own waffles along with cereal, toast, etc. The room was very clean. The only criticism is that the heating/air conditioning unit in the room was loud. I don't know if it was just my room but I turned it off due to the noise when sleeping."

Hilton Garden Inn Solomons

8/10 Good

"The room was clean and away from the elevators with no issues for the specific room. The only reason this is not a 5 star review is that there is no accommodation for customers / guests that need a nightstand on both sides of the bed. In our situation both customers have a CPAP machine. The reservation was for 2 guests and the room was a queen bed and upon arrival we had to decide who was going to sleep without their CPAP machine because the room has no bedside table or electrical outlets on the outer edge of the bed. Regardless of the medical need when will Hotels learn that both sides of the bed need a place to hold their CPAP or book or tea."

Find out more about Leonardtown

Everything you need to know about Leonardtown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Leonardtown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Leonardtown vacation 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 low season months. For more hustle and bustle, you may prefer to visit Leonardtown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $266 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Leonardtown rentals

At Expedia, we put the best Leonardtown vacation 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 vacation.

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.

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Things to do in Maryland

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.

Leonardtown Vacation Rentals

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Check prices for these dates

Our top choices for Leonardtown vacation rentals

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

2. 2 Acre Oasis with Private Beach! Family and dog friendly!

3. Coles Point Marina

4. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

5. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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

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

8. Cozy Virginia Potomac Riverfront Cottage

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

10. Just a getaway piece of property

11. 4-BR Waterfront Turret Home

12. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

13. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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

15. Sail Away

16. Bright and airy waterfront getaway

17. Riverfront Home w/Dock · Fire Pit · Kids Play Area

18. Charming Waterfront 3-bedroom house in Piney Point

19. 2 Bedroom Cottage at Coles Point Marina

20. 1 m. to Beaches & Town, Grill, Deck, Outdoor Seating

Find vacation rentals that suit your style

Top Leonardtown Hotel Reviews

Holiday Inn Express and Suites King George- Dahlgren by IHG

Find out more about Leonardtown

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