Leonardtown Vacation Rentals from $261: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Leonardtown vacation rentals

Coffee/tea maker, fridge, microwave, oven

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

Leonardtown

Christy C.

$547 nightly

Sep 13 - Sep 14

Total with taxes and fees

2. Coles Point Marina

Hague

$255 nightly

Oct 5 - Oct 6

Total with taxes and fees

3. Cozy Virginia Potomac Riverfront Cottage

Hague

Ashley D.

$315 nightly

Sep 10 - Sep 11

Total with taxes and fees

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

Benedict

ed r.

$241 nightly

Sep 10 - Sep 11

Total with taxes and fees

5. Soul Oasis - home on the Chesapeake Bay

Lusby

Dusty S.

$278 nightly

Oct 7 - Oct 8

Total with taxes and fees

6. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Montross

Julie P.

$439 nightly

Sep 13 - Sep 14

Total with taxes and fees

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

Colonial Beach

Amy H.

$224 nightly

Sep 10 - Sep 11

Total with taxes and fees

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

Saint Leonard

Nancy P.

$246 nightly

Sep 16 - Sep 17

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cottages

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Leonardtown Hotel Reviews

avid hotel California - Lexington Park by IHG

10/10 Excellent

"Great stay! Staff was super friendly and rooms are definitely soundproof!! My super noisy 3 year old was VERY noisy and we were surprised and delighted to not be disrupting other people’s stays!!"

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

10/10 Excellent

"My family and I had a great stay at this LaQuinta location for a funeral . David was such a great help checking us in. There were lots of shopping and restaurants near by to choose from if needed. The rooms were roomy and clean."

Hampton Inn by Hilton Lexington Park

8/10 Good

"Arrived for check in & grabbed the keys without checking the room. Upon return (much later that evening/early morning hours) I entered the room to find it wasn’t what I booked. Didn’t have sofa bed as advertised, so I head to the front desk. The lady ignored me ringing the bell, ignored me calling the front desk phone & remained in the room with the camera footage. Eventually she emerged & gave me nothing but a hard time. I informed her there was no where for my children to sleep & showed her my booking. She continually said she couldn’t override to move my room. About 15 minutes later she magically gave me new keys to another room. Place is clean, well kept & local to food/gas, etc. This may have been a one off situation but it was not handled well."

Quality Inn Solomons - Beacon Marina

8/10 Good

"Everything was good, standard hotel/motel stuff: little coffee pot, mini-fridge, microwave, tv,a/c - everything worked as expected, furniture, carpeting, lights, bathroom all looked newish and everything was very clean. Desk folk were pleasant, didn’t have much interaction. The big plus is the location, right by a huge marina (if you like looking at boats) and the Calvert Marine Museum- combines natural history and the commercial history of the area, has the Drum Point lighthouse (you can tour) and a boat tour of Patuxent Harbor, plus fossils, river otters, fish. Calvert Cliffs / Flag Pond parks are a 10 minute drive if you want to dig for fossils yourself. So: comfortable place, very reasonably priced, close to all sorts of stuff; definitely worth it."

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 $261 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.

Explore a world of travel with Expedia

Things to do in Maryland

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?

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 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 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

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Leonardtown vacation rentals

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

2. Coles Point Marina

3. Cozy Virginia Potomac Riverfront Cottage

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

5. Soul Oasis - home on the Chesapeake Bay

6. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

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

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

9. Bright and airy waterfront getaway

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

11. 7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away

12. Sail Away To

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

14. 4-BR Waterfront Turret Home

15. 2 Bedroom Cottage at Coles Point Marina

16. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

17. Charming Waterfront 3-bedroom house in Piney Point

18. Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

19. River Refresh - Waterfront with Spa on Placid Bay

20. Lakefront Cabin Near Solomons Island w/ Hot Tub

Find vacation rentals that suit your style

Top Leonardtown Hotel Reviews

avid hotel California - Lexington Park by IHG

Find out more about Leonardtown

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app