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 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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.
$539 nightly
The price is $570
Aug 2 - Aug 3
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
$295 nightly
The price is $321
Aug 3 - Aug 4
Total with taxes and fees
Coles Point Marina
Interior

3. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (50 reviews)
"Wonderful views, clean home and quaint ! We highly recommend!"
United States
Tim R.
$315 nightly
The price is $343
Aug 3 - Aug 4
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
Exterior

4. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
$283 nightly
The price is $300
Aug 24 - Aug 25
Total with taxes and fees
Soul Oasis - home on the Chesapeake Bay
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
$241 nightly
The price is $266
Aug 3 - Aug 4
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, (68 reviews)
"Always a great stay! "
United States
Amy H.
$246 nightly
The price is $268
Aug 18 - Aug 19
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, (3 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
$256 nightly
The price is $272
Aug 18 - Aug 19
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Interior

8. 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, (11 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
$373 nightly
The price is $375
Aug 25 - Aug 26
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Exterior

9. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$389 nightly
The price is $423
Aug 2 - Aug 3
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
Interior

10. Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
10.0 out of 10, Exceptional, (1 review)
"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."
United States
Paige
$502 nightly
The price is $546
Aug 18 - Aug 19
Total with taxes and fees
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Property grounds

11. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (21 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
$349 nightly
The price is $369
Aug 3 - Aug 4
Total with taxes and fees
Bright and airy waterfront getaway
Property grounds

12. Sail Away

Sail Away
Colonial Beach
10.0 out of 10, Exceptional, (12 reviews)
"we liked everything and location!!!"
United States
Shawn
$309 nightly
The price is $312
Aug 26 - Aug 27
Total with taxes and fees
Sail Away
Sun loungers, beach towels

13. 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.
$955 nightly
The price is $1,039
Aug 2 - Aug 3
Total with taxes and fees
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Smart TV, books

14. 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.
$697 nightly
The price is $770
Aug 9 - Aug 10
Total with taxes and fees
4-BR Waterfront Turret Home
Property grounds

15. 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.
$416 nightly
The price is $463
Aug 9 - Aug 10
Total with taxes and fees
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Exterior

16. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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 3 - Aug 4
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
Outdoor dining

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

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (38 reviews)
"The host went above and beyond to make us feel welcome. From the smooth check-in to the thoughtful welcome basket, every detail was handled with care. We especially loved the riverfront home and all the commodities included. A true home away from home!"
United States
Evelyn C.
$582 nightly
The price is $634
Aug 24 - Aug 25
Total with taxes and fees
Waterfront Reset: Views, Games, Boats & Total Calm
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.
$491 nightly
The price is $534
Aug 2 - Aug 3
Total with taxes and fees
River Refresh - Waterfront with Spa on Placid Bay
Coffee/tea maker, fridge, microwave, oven

19. 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.
$654 nightly
The price is $711
Aug 4 - Aug 5
Total with taxes and fees
Riverfront Home w/Dock · Fire Pit · Kids Play Area
Dining

20. 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)
"Hosts were very helpful. The cottage is adorable and well maintained. "
United States
William L.
$382 nightly
The price is $422
Aug 31 - Sep 1
Total with taxes and fees
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
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

My Place Hotel - Dahlgren/King George, VA

My Place Hotel - Dahlgren/King George, VA

8/10 Good
"very clean rooms with refrigerator, microwave, coffee maker and stovetop. Staff was very friendly."
Diane 2-night trip
Posted 12 hours ago
My Place Hotel - Dahlgren/King George, VA

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 $268 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?

Charming Waterfront Farmhouse 10 minutes from Blackwater NWR - Pet Friendly: This vacation home rental near Leonardtown is located on a river and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

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?

Abell's Wharf and St. Mary's River State Park are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Leonardtown Park 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.