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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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.
The price is CA $340
CA $833 total
includes taxes & fees
Oct 11 - Oct 12
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, (66 reviews)
"Beautiful location "
United States
Jonathan M.
The price is CA $563
CA $1,203 total
includes taxes & fees
Oct 26 - Oct 27
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
The price is CA $196
CA $345 total
includes taxes & fees
Oct 8 - Oct 9
Coles Point Marina
A coastal area with a sandy beach, a small settlement, and a clear view of the sea.

4. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is CA $234
CA $658 total
includes taxes & fees
Oct 8 - Oct 9
Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK
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
9.2 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.
The price is CA $218
CA $383 total
includes taxes & fees
Oct 8 - Oct 9
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
A wooden cabin with a balcony, surrounded by lush greenery and trees.

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.
The price is CA $153
CA $366 total
includes taxes & fees
Oct 12 - Oct 13
Rest & Recharge, A-frame Cabin on Winery Grounds
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

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, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is CA $178
CA $378 total
includes taxes & fees
Oct 20 - Oct 21
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Private kitchen

8. 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.
The price is CA $224
CA $324 total
includes taxes & fees
Oct 12 - Oct 13
Just a getaway piece of property
A spacious living room with a large sofa, a television, and a view of the ocean.

9. 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.
The price is CA $426
CA $1,057 total
includes taxes & fees
Oct 14 - Oct 15
4-BR Waterfront Turret Home
A covered patio with a view of a lake, furnished with chairs and a table.

10. 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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $284
CA $587 total
includes taxes & fees
Oct 20 - Oct 21
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A backyard with a fire pit surrounded by green Adirondack chairs, a wooden fence, and a house with string lights.

11. 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
9.6 out of 10, Exceptional, (16 reviews)
"Great place, super cute and walking distance to everything. Host was great!"
United States
Crystal W.
The price is CA $156
CA $520 total
includes taxes & fees
Oct 28 - Oct 29
7 Min to Beach, Huge Yard, Fire Pit, BBQ, Beach Gear & Cornhole, by A Haven Away
A single-story house with a front porch, a small deck, and a number '4' on the side.

12. 2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is CA $490
CA $608 total
includes taxes & fees
Oct 11 - Oct 12
2 Bedroom Cottage at Coles Point Marina
A two-story house with a balcony, surrounded by trees and a wooden fence.

13. 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
The price is CA $438
CA $1,087 total
includes taxes & fees
Oct 19 - Oct 20
Charming Waterfront 3-bedroom house in Piney Point
An outdoor patio with a glass table and chairs, a blue umbrella, and a view of a lake.

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.
The price is CA $300
CA $689 total
includes taxes & fees
Oct 28 - Oct 29
Waterfront Game-Themed Getaway · Dock & Kayaks
A waterfront hotel with a dock extending into the water, a large building with multiple floors, and a clear sky.

15. Sail Away To

Sail Away To
Colonial Beach
9.6 out of 10, Exceptional, (18 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
The price is CA $190
CA $444 total
includes taxes & fees
Oct 12 - Oct 13
Sail Away To
A lakeside view with chairs and a table, a rainbow, and trees.

16. 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
The price is CA $295
CA $505 total
includes taxes & fees
Oct 8 - Oct 9
Bright and airy waterfront getaway
A modern kitchen with grey cabinets, a large island with bar stools, and a view of the living area.

17. 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.
Riverfront Home w/Dock · Fire Pit · Kids Play Area
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

18. 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, (3 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $657
CA $1,410 total
includes taxes & fees
Oct 14 - Oct 15
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A pathway lined with trees and lights leading to a wooden building with a visible window.

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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is CA $657
CA $1,226 total
includes taxes & fees
Oct 16 - Oct 17
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

20. 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.
The price is CA $654
CA $1,702 total
includes taxes & fees
Oct 12 - Oct 13
Lakefront Cabin Near Solomons Island w/ Hot Tub
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

Island Inn & Suites, an Ascend Collection Hotel

Island Inn & Suites, an Ascend Collection Hotel

10/10 Excellent
"Nice staff and clean and quiet hotel. Literally right on the water in a fairly remote location. Highly recommended."
Michael 1-night trip
Posted 8 hours ago
Island Inn & Suites, 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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Leonardtown vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Leonardtown vacation rentals we have selected for you start as low as CA $366 per night. Entering your travel dates in the search wizard 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 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.