Leonardtown Vacation Rentals

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Check prices for these dates

In two weeks
May 1 - May 3
In two months
Jun 12 - Jun 14
In three months
Jul 10 - Jul 12
In four months
Aug 7 - Aug 9

Our top choices for Leonardtown vacation rentals

Fridge, microwave, oven, stovetop

Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.4 out of 10, Exceptional, (6 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is ￥35,836
￥88,769 total
includes taxes & fees
Apr 14 - Apr 15
Anne & Fred`s Leonardtown Home W/ Arcade room!
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is ￥30,261
￥69,473 total
includes taxes & fees
Apr 14 - Apr 15
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Exterior

Rest & Recharge, A-frame Cabin on Winery Grounds

Rest & Recharge, A-frame Cabin on Winery Grounds
Colonial Beach
9.8 out of 10, Exceptional, (60 reviews)
"Very quiet and great location."
United States
Cindy B.
The price is ￥17,631
￥40,673 total
includes taxes & fees
Apr 15 - Apr 16
Rest & Recharge, A-frame Cabin on Winery Grounds
Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (44 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is ￥20,068
￥44,908 total
includes taxes & fees
Apr 21 - Apr 22
Soul Oasis - home on the Chesapeake Bay
Property grounds

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, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is ￥24,368
￥42,045 total
includes taxes & fees
Apr 14 - Apr 15
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Smart TV

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear

7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Colonial Beach
9.4 out of 10, Exceptional, (12 reviews)
"We stayed for 2 nights in the fall for a family event at Stratford Harbor. The house was pristine and cozy. Loved the fenced backyard for the pets and the walk ability of the town. The host and back up host were VERY responsive."
United States
Saundra B.
The price is ￥14,062
￥53,940 total
includes taxes & fees
Apr 14 - Apr 15
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Property grounds

Sail Away

Sail Away
Colonial Beach
9.8 out of 10, Exceptional, (9 reviews)
"Stay was wonderful!"
United States
Karen H.
The price is ￥18,794
￥46,322 total
includes taxes & fees
Apr 15 - Apr 16
Sail Away
Smart TV, books

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
9.8 out of 10, Exceptional, (6 reviews)
"Our family had a great stay. Thank you!"
United States
Colleen G.
The price is ￥32,650
￥67,699 total
includes taxes & fees
Apr 14 - Apr 15
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Sun loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is ￥42,286
￥50,226 total
includes taxes & fees
Apr 14 - Apr 15
Cottage Located on the Patuxent River!
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥37,965
￥69,575 total
includes taxes & fees
Apr 14 - Apr 15
Coles Point Marina
Outdoor dining

Dock+Boats+Firepit: Game Theme Waterfront Retreat

Dock+Boats+Firepit: Game Theme Waterfront Retreat
Montross
10.0 out of 10, Exceptional, (31 reviews)
"Great spot"
United States
SHAWN W.
The price is ￥35,090
￥79,525 total
includes taxes & fees
Apr 15 - Apr 16
Dock+Boats+Firepit: Game Theme Waterfront Retreat
TV, books, stereo

River Refresh - Waterfront with Spa on Placid Bay

River Refresh - Waterfront with Spa on Placid Bay
Colonial Beach
10.0 out of 10, Exceptional, (22 reviews)
"Fantastic amenities, beautiful view, cosy yet spacious!"
United States
Aaron M.
The price is ￥39,818
￥84,393 total
includes taxes & fees
Apr 14 - Apr 15
River Refresh - Waterfront with Spa on Placid Bay
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (10 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is ￥42,525
￥79,348 total
includes taxes & fees
Apr 15 - Apr 16
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Dining

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

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (12 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is ￥37,428
￥71,410 total
includes taxes & fees
Apr 24 - Apr 25
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Smart TV, books

4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is ￥55,745
￥118,767 total
includes taxes & fees
Apr 14 - Apr 15
4-BR Waterfront Turret Home
Interior

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, (7 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is ￥29,465
￥62,883 total
includes taxes & fees
Apr 20 - Apr 21
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Sun loungers, beach towels

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is ￥28,490
￥77,093 total
includes taxes & fees
Apr 14 - Apr 15
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Fridge, microwave, oven, stovetop

Luxury Modern Waterfront Retreat

Luxury Modern Waterfront Retreat
Montross
9.6 out of 10, Exceptional, (15 reviews)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is ￥25,005
￥74,689 total
includes taxes & fees
Apr 16 - Apr 17
Luxury Modern Waterfront Retreat
Terrace/patio

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Heathsville
9.6 out of 10, Exceptional, (33 reviews)
"We loved the tranquility of the place, beautiful views, and the unique design of the house. The host was very responsive. It was a very relaxing stay. I am sure we will be coming back soon."
United States
Liudmila U.
The price is ￥33,112
￥99,305 total
includes taxes & fees
Apr 14 - Apr 15
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
House (3 Bedrooms) | Interior

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
Lusby
The price is ￥38,066
￥110,916 total
includes taxes & fees
Apr 14 - Apr 15
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
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 Prince Frederick by IHG

Holiday Inn Express Prince Frederick by IHG

6/10 Okay
"Room was ok, not too dirty but definitely outdated..floors could be better. Couldn’t find staff around 6:30am to check out so I left my room keys on their laptop. "
Calista 1-night trip
Posted 2 hours ago
Holiday Inn Express Prince Frederick by IHG

Find out more about Leonardtown

Search for holiday rentals in Leonardtown on Expedia! You can easily find your home rentals, villas, holiday apartments in Leonardtown using one of the methods below:

  • View our selection of featured holiday rentals in Leonardtown
  • Use the map to find apartments and other holiday homes in the Leonardtown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Leonardtown while they last

Look no further and take a look at our great range of rental properties in Leonardtown!

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?

Quaint waterfront home with private beach: This vacation home rental near Leonardtown is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a patio and a selection of games.

How many vacation rentals will I find in Leonardtown?

With 11 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 lovely local spots to get outside and enjoy nature. 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.