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

Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Leonardtown vacation rentals

Coffee/tea maker, fridge, microwave, oven

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.
$556 nightly
The price is $589
Aug 17 - Aug 18
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
Cottage, 2 Bedrooms, Kitchen | Exterior

2. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
$323 nightly
The price is $352
Aug 17 - Aug 18
Total with taxes and fees
Coles Point Marina
Exterior

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute A-frame with all the necessities!"
United States
Anonymous traveler
$289 nightly
The price is $306
Sep 8 - Sep 9
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Interior

4. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (53 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.
$315 nightly
The price is $343
Aug 17 - Aug 18
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
Property grounds

5. 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
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
$244 nightly
The price is $269
Aug 19 - Aug 20
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

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.
$241 nightly
The price is $262
Aug 25 - Aug 26
Total with taxes and fees
Rest & Recharge, A-frame Cabin on Winery Grounds
TV, fireplace

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, (6 reviews)
"Lovely!! Perfect for our family for a weekend adventure. Very fun spaces with everything you need. The morning stroll to see the sunrise over the water was divine! Thank you!"
United States
Kate J.
$260 nightly
The price is $276
Aug 18 - Aug 19
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Property grounds

8. 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)
"This place is fantastic!!Great responsive owners! Fantastic location, perfectly stocked kitchen, comfy beds and bar none the cleanest place I’ve stayed!! The house is adorable and comfortable with a rocking fire pit. The location is walkable and yet quiet!Stay here!No notes!!"
United States
Amanda M.
$302 nightly
The price is $337
Sep 8 - Sep 9
Total with taxes and fees
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Interior

9. 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, (12 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
$383 nightly
The price is $386
Sep 14 - Sep 15
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Smart TV, books

10. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$657 nightly
The price is $725
Sep 8 - Sep 9
Total with taxes and fees
4-BR Waterfront Turret Home
Property grounds

11. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$353 nightly
The price is $374
Aug 25 - Aug 26
Total with taxes and fees
Bright and airy waterfront getaway
Property grounds

12. Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (13 reviews)
"we liked everything and location!!!"
United States
Shawn
$331 nightly
The price is $336
Aug 31 - Sep 1
Total with taxes and fees
Sail Away
Dining

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy and comfortable."
United States
sandi c.
$318 nightly
The price is $351
Aug 17 - Aug 18
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Outdoor dining

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

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (38 reviews)
"What a lovely weekend. Beautiful views, winery at Ingleside , breakfast and shopping in Warsaw, grilling and paddle boating. Thank you. It was just what we needed!!’"
United States
Diana H.
$546 nightly
The price is $594
Sep 16 - Sep 17
Total with taxes and fees
Waterfront Reset: Views, Games, Boats & Total Calm
Exterior

15. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (5 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
$723 nightly
The price is $798
Aug 19 - Aug 20
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
Coffee/tea maker, fridge, microwave, oven

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, (16 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.
$529 nightly
The price is $575
Sep 8 - Sep 9
Total with taxes and fees
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Interior

17. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
$1,041 nightly
The price is $1,150
Aug 24 - Aug 25
Total with taxes and fees
Lakefront Cabin Near Solomons Island w/ Hot Tub
Exterior

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.
$479 nightly
The price is $521
Aug 19 - Aug 20
Total with taxes and fees
River Refresh - Waterfront with Spa on Placid Bay
Property grounds

19. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
$742 nightly
The price is $786
Aug 26 - Aug 27
Total with taxes and fees
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake 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

Comfort Inn & Suites Lexington Park near Pax River

Comfort Inn & Suites Lexington Park near Pax River

10/10 Excellent
"The hotel stay was perfect for me. I needed a hotel close to PAX Navel Air Station and it couldn’t be closer. Friendly efficient staff. A very clean and well maintained hotel. My included breakfast was quite adequate for me. A good stay."
Patti 2-night trip
Posted 3 hours ago
Comfort Inn & Suites Lexington Park near Pax River

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 $269 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

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?

Updated home 2 blocks from water in Colonial Beach-come visit Driftwood Cottage!: This vacation home rental near Leonardtown offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Leonardtown?

With 10 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 Leonardtown Library 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.