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

Leonardtown Vacation Rentals

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Dates

November 2026

December 2026

Check prices for these dates

In two weeks

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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.

$524 nightly

Nov 9 - Nov 10

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.

$720 nightly

Dec 1 - Dec 2

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

Nov 9 - Nov 10

Total with taxes and fees

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

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

Colonial Beach

Amy H.

$230 nightly

Nov 30 - Dec 1

Total with taxes and fees

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

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

Benedict

ed r.

$248 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

6. Cozy Virginia Potomac Riverfront Cottage

Hague

Carmelita A.

$299 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

7. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Montross

Julie P.

$472 nightly

Nov 9 - Nov 10

Total with taxes and fees

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

8. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Saint Leonard

Nancy P.

$269 nightly

Nov 16 - Nov 17

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.

9. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

Colonial Beach

Crystal W.

$275 nightly

Nov 8 - Nov 9

Total with taxes and fees

10. Just a getaway piece of property

Mechanicsville

David L.

$199 nightly

Nov 15 - Nov 16

Total with taxes and fees

A covered patio with a view of a lake, furnished with chairs and a table.

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

Lexington Park

Andrea B.

$377 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

12. 4-BR Waterfront Turret Home

Solomons

Thomas S.

$635 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

13. Sail Away

Colonial Beach

Shawn

$288 nightly

Nov 30 - Dec 1

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.

$424 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

15. Bright and airy waterfront getaway

Benedict

George

$345 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

16. Charming Waterfront 3-bedroom house in Piney Point

Piney Point

Meira

$625 nightly

Nov 8 - Nov 9

Total with taxes and fees

17. 2 Bedroom Cottage at Coles Point Marina

Hague

$372 nightly

Nov 6 - Nov 7

Total with taxes and fees

A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

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

Montross

N C.

$460 nightly

Nov 9 - Nov 10

Total with taxes and fees

A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

19. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Prince Frederick

Sean B.

$375 nightly

Nov 20 - Nov 21

Total with taxes and fees

A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

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

Lusby

Dani B.

$921 nightly

Nov 10 - Nov 11

Total with taxes and fees

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Find vacation rentals that suit your style

Top Leonardtown Hotel Reviews

A spacious lobby with a reception desk, seating area, and large windows.

The Inn at Leonardtown, an Ascend Collection Hotel

Leonardtown

10/10 Excellent

Edward

A modern hotel with a prominent 'avid' sign, large windows, and a covered outdoor seating area.

avid hotel California - Lexington Park by IHG

California

10/10 Excellent

Elizabeth

A hotel room with a large bed, a nightstand with a lamp, a brown sofa, and artwork on the wall.

Sleep Inn & Suites California MD

California

10/10 Excellent

Cynthia

A hotel lobby with a dining area, seating, a fireplace, and a view of the outside through large windows.

Hampton Inn by Hilton Lexington Park

Lexington Park

10/10 Excellent

Jen

An outdoor seating area with a fire pit, cushioned benches, and a modern design.

Home2 Suites by Hilton Lexington Park Patuxent River NAS, MD

Lexington Park

10/10 Excellent

A modern hotel lobby with seating areas, a reception desk, and a staircase.

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

California

10/10 Excellent

Octavia

A hotel lobby with wooden doors, a reception desk, and a seating area with tables and chairs.

Comfort Inn & Suites Lexington Park near Pax River

Lexington Park

10/10 Excellent

I just joined a colleague at this hotel after his selection, but it was a great experience, and this was a first-time, three night stay. First, for a budget hotel, they have an acceptable gym with one ea. tread, elliptical, bike plus a multi-station; they also advertise (though I didn't get to it) an agreement with a local regular gym should you be interested. Well located for fast foods, and perfect for quick access to NAS Pax Gate 2. Rooms were large, internet worked, breakfast was pretty huge...

Anonymous traveler

A Fairfield by Marriott Inn & Suites building with a covered entrance, multiple windows, and a parking lot.

Fairfield Inn by Marriott Lexington Park Patuxent River Naval Air Station

Lexington Park

10/10 Excellent

Kathleen

A wooden chair on a balcony overlooking a sunset over a body of water.

Island Inn & Suites, an Ascend Collection Hotel

Piney Point

10/10 Excellent

I usually stay in Solomons but when I found this hotel I will never go back to Solomons. What a beautiful location. All the rooms are water front and super clean. The restaurant bar next door offers a good variety of choices that are reasonably priced. I had the crab cake, it was the best I have ever had. I was worried about the distance but it actually took me less time to get to the hotel than it usually does Solomons. I understand why the call it Maryland's best kept secret. Service was...

OnTheRoadAgain2much

My Place Hotel - Dahlgren/King George, VA

King George

10/10 Excellent

Dianne

A covered outdoor seating area with wicker furniture and large windows.

Hilton Garden Inn Solomons

Solomons

10/10 Excellent

Anonymous traveler

A Holiday Inn Express & Suites building with a covered entrance and multiple parking spaces.

Holiday Inn Express and Suites King George- Dahlgren by IHG

King George

10/10 Excellent

The Hotel is realitively new and everything is clean and in great working order. The shower had three cannisters mounted on the wall for dispersing shampoo, conditioner and body soap. The bed was comfortable with an ample number of pillows. There are plenty of lights spread throughout the room. The breakfast was good with a decent selection of hot food (eggs, great bacon, pancakes, cereals and toast) along with a broad selection of drinks. Hotel is in a good location in the Dahlgren, Va. area,...

Anonymous traveler

A Holiday Inn Express hotel with a modern facade, a prominent sign, and a well-lit entrance.

Holiday Inn Express Prince Frederick by IHG

Prince Frederick

10/10 Excellent

Troy

A beachside view with a wooden deck, tables, and chairs, overlooking a sandy beach and calm sea.

Colonial Beach Plaza Bed & Breakfast

Colonial Beach

10/10 Excellent

Jeremy

A garden with pink flowers and a bench by the water.

River Edge Inn

Colonial Beach

10/10 Excellent

Desiree

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 $219 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.

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.

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