Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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!

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.
$524 nightly
The price is $555
Nov 9 - Nov 10
Total with taxes and fees
Anne & Fred`s Leonardtown Home W/ Arcade room!
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!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
$720 nightly
The price is $796
Dec 1 - Dec 2
Total with taxes and fees
2 Acre Oasis with Private Beach! Family and dog friendly!
A single-story house with a front porch, a small deck, and a number '4' on the side.

3. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
10.0 out of 10, Exceptional, (1 review)
"If you want a quiet slice of VA/Potomac waterfront, this is the place."
United States
John
$255 nightly
The price is $278
Nov 9 - Nov 10
Total with taxes and fees
Coles Point Marina
A wooden cabin with a sloped roof, surrounded by trees and a hammock.

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

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (76 reviews)
"Always a great stay! "
United States
Amy H.
$230 nightly
The price is $251
Nov 30 - Dec 1
Total with taxes and fees
Rest & Recharge, A-frame Cabin on Winery Grounds
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.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
$248 nightly
The price is $274
Nov 10 - Nov 11
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A room with a large window overlooking a beach with a wooden pier and lounge chairs.

6. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (56 reviews)
"My family and I had a great time at this property fishing and crabbing. We also did a day trip to Westmoreland State Park, where we got to hike to Fossils Beach."
United States
Carmelita A.
$299 nightly
The price is $325
Nov 6 - Nov 7
Total with taxes and fees
Cozy Virginia Potomac Riverfront Cottage
A modern kitchen with stainless steel appliances, a central island, and a dining area with a view of the outdoors.

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

Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Montross
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
$472 nightly
The price is $506
Nov 9 - Nov 10
Total with taxes and fees
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
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

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.
$269 nightly
The price is $285
Nov 16 - Nov 17
Total with taxes and fees
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
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

7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Colonial Beach
9.4 out of 10, Exceptional, (17 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
$275 nightly
The price is $306
Nov 8 - Nov 9
Total with taxes and fees
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
Private kitchen

10. 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.
$199 nightly
The price is $220
Nov 15 - Nov 16
Total with taxes and fees
Just a getaway piece of property
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

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (20 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
$377 nightly
The price is $379
Nov 9 - Nov 10
Total with taxes and fees
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A spacious living room with a large sofa, a television, and a view of the ocean.

12. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
$635 nightly
The price is $703
Nov 9 - Nov 10
Total with taxes and fees
4-BR Waterfront Turret Home
A balcony with a white railing, outdoor furniture, and a view of the sea.

13. Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (14 reviews)
"we liked everything and location!!!"
United States
Shawn
$288 nightly
The price is $290
Nov 30 - Dec 1
Total with taxes and fees
Sail Away
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

Waterfront Reset: Views, Games, Boats & Total Calm
Montross
10.0 out of 10, Exceptional, (40 reviews)
"We really enjoyed our stay at this lake house. The view is beautiful and the house is beautifully decorated and kid friendly. Just a really charming place to stay for a family vacation."
United States
Nicole P.
$424 nightly
The price is $462
Nov 17 - Nov 18
Total with taxes and fees
Waterfront Reset: Views, Games, Boats & Total Calm
A lakeside view with chairs and a table, a rainbow, and trees.

15. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 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
$345 nightly
The price is $366
Nov 10 - Nov 11
Total with taxes and fees
Bright and airy waterfront getaway
A two-story house with a balcony, surrounded by trees and a wooden fence.

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, (9 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
$625 nightly
The price is $691
Nov 8 - Nov 9
Total with taxes and fees
Charming Waterfront 3-bedroom house in Piney Point
A single-story house with a front porch, a small deck, and a number '4' on the side.

17. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
$372 nightly
The price is $405
Nov 6 - Nov 7
Total with taxes and fees
2 Bedroom Cottage at Coles Point Marina
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

Riverfront Home w/Dock · Fire Pit · Kids Play Area
Montross
9.6 out of 10, Exceptional, (18 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.
$460 nightly
The price is $501
Nov 9 - Nov 10
Total with taxes and fees
Riverfront Home w/Dock · Fire Pit · Kids Play Area
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.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
$375 nightly
The price is $398
Nov 20 - Nov 21
Total with taxes and fees
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
$921 nightly
The price is $925
Nov 10 - Nov 11
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

A spacious lobby with a reception desk, seating area, and large windows.
The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel
Leonardtown

10/10 Excellent

A clean, pleasant hotel with lots of light and friendly staff in the middle of little Leonardtown. I actually asked the front desk if they were new because of how clean everything was and they said they did a major renovation about 5 years ago. Easy (and FREE) parking across the street. Our room (a king bed) was clean and quiet. If we're ever in the area again, this is where we'd stay.
United States
Edward
Reviewed October 1, 2026
The Inn at Leonardtown, an Ascend Collection Hotel

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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