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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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.
$526 nightly
The price is $557
Sep 21 - Sep 22
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
TV, fireplace

2. 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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$234 nightly
The price is $248
Sep 23 - Sep 24
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Exterior

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (63 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
$277 nightly
The price is $294
Sep 30 - Oct 1
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
Cottage, 2 Bedrooms, Kitchen | Exterior

4. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
$255 nightly
The price is $278
Oct 5 - Oct 6
Total with taxes and fees
Coles Point Marina
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
9.2 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.
$241 nightly
The price is $266
Sep 21 - Sep 22
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Property grounds

6. 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.
$281 nightly
The price is $313
Sep 23 - Sep 24
Total with taxes and fees
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Interior

7. 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.
$315 nightly
The price is $343
Sep 21 - Sep 22
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
Sun loungers, beach towels

8. 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.
$440 nightly
The price is $471
Sep 28 - Sep 29
Total with taxes and fees
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Private kitchen

9. Just a getaway piece of property

Just a getaway piece of property
Mechanicsville
10.0 out of 10, Exceptional, (1 review)
"Perfect place. Just what i was looking. Definitely recommend to anyone looking to stay close to the MIR track for any event"
United States
David L.
$209 nightly
The price is $230
Sep 25 - Sep 26
Total with taxes and fees
Just a getaway piece of property
Beach

10. 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
$301 nightly
The price is $305
Oct 6 - Oct 7
Total with taxes and fees
Sail Away To
Interior

11. 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.
$363 nightly
The price is $365
Sep 28 - Sep 29
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Exterior

12. 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.
$233 nightly
The price is $254
Oct 12 - Oct 13
Total with taxes and fees
Rest & Recharge, A-frame Cabin on Winery Grounds
Property grounds

13. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (24 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
$335 nightly
The price is $355
Sep 21 - Sep 22
Total with taxes and fees
Bright and airy waterfront getaway
Outdoor dining

14. Waterfront Game-Themed Getaway · Dock & Kayaks

Waterfront Game-Themed Getaway · Dock & Kayaks
Montross
10.0 out of 10, Exceptional, (40 reviews)
"Very comfortable beds and living spaces, and can accommodate large groups and handicapped!"
United States
Amanda B.
$496 nightly
The price is $540
Oct 6 - Oct 7
Total with taxes and fees
Waterfront Game-Themed Getaway · Dock & Kayaks
Smart TV, books

15. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$623 nightly
The price is $689
Sep 21 - Sep 22
Total with taxes and fees
4-BR Waterfront Turret Home
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, (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.
$501 nightly
The price is $545
Sep 22 - Sep 23
Total with taxes and fees
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Exterior

17. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$389 nightly
The price is $423
Sep 21 - Sep 22
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
Property grounds

18. Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (13 reviews)
"we liked everything and location!!!"
United States
Shawn
$317 nightly
The price is $321
Sep 23 - Sep 24
Total with taxes and fees
Sail Away
Exterior

19. 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
$683 nightly
The price is $754
Oct 19 - Oct 20
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
TV, fireplace, video games, books

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

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
$951 nightly
The price is $956
Sep 29 - Sep 30
Total with taxes and fees
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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

Holiday Inn Express and Suites King George- Dahlgren by IHG

Holiday Inn Express and Suites King George- Dahlgren by IHG

8/10 Good
"Very clean and in a good location!! Just stayed the weekend but enjoyed it very much!!"
Daniel W 2-night trip
Posted 1 hour ago
Holiday Inn Express and Suites King George- Dahlgren by IHG

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 $248 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 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 Abell's Wharf are a couple of scenic spots to enjoy the outdoors, whereas North End Gallery is one of the cultural attractions. 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.