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Leonardtown Holiday Rentals

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Check prices for these dates

Tonight
16 Jul - 17 Jul
Tomorrow
17 Jul - 18 Jul
This weekend
18 Jul - 20 Jul
Next weekend
25 Jul - 27 Jul

Holiday Rentals in Leonardtown

Anne & Fred's Leonardtown Home
Enjoy cooking in this well-lit kitchen with a microwave, oven, and dishwasher.

Anne & Fred's Leonardtown Home

9.4 out of 10, Exceptional, (3)
"Nice place to stay. Perfect location for our needs. Suggest noting the hot and cold water flip upstairs, and to add a mirror in the hallway by outlet for blow dryer."
The price is NZ$918
includes taxes & fees
20 July - 21 July
Anne & Fred's Leonardtown Home
Charming 1-bedroom house with AC and WiFi in quaint Montross
Relax on the covered porch with four comfortable chairs and a charming garden.

Charming 1-bedroom house with AC and WiFi in quaint Montross

10.0 out of 10, Exceptional, (8)
"Perfect spot for our weekend away! Excellent location to hit multiple spots in the area. Clean, quiet and cozy, 10/10 would recommend. We are already planning our next trip! "
The price is NZ$414
includes taxes & fees
17 July - 18 July
Charming 1-bedroom house with AC and WiFi in quaint Montross
River Refresh - Waterfront with Spa on Placid Bay
Enjoy a serene waterfront view from this deck, surrounded by lush greenery and trees, with a table and chairs perfect for outdoor dining.

River Refresh - Waterfront with Spa on Placid Bay

10.0 out of 10, Exceptional, (14)
"Wonderful getaway! "
The price is NZ$869
includes taxes & fees
28 July - 29 July
River Refresh - Waterfront with Spa on Placid Bay
Riverside Dreams -golfcart-views-screened porch-
Enjoy cooking in this well-equipped kitchen with oven, microwave, sink, and dishwasher.

Riverside Dreams -golfcart-views-screened porch-

2.0 star property
10.0 out of 10, Exceptional, (2)
"We found the view and the accommodations quite lovely."
The price is NZ$774
includes taxes & fees
22 July - 23 July
Riverside Dreams -golfcart-views-screened porch-
Waterfront home where you can relax or enjoy the things the Northern Neck.
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and countertop appliances.

Waterfront home where you can relax or enjoy the things the Northern Neck.

9.8 out of 10, Exceptional, (9)
"Sandy was a wonderful and very responsive host. She made sure we felt very welcomed and 'at home' in this lovely house on the water. The home and owners made this a trip we'll remember."
The price is NZ$507
includes taxes & fees
21 July - 22 July
Waterfront home where you can relax or enjoy the things the Northern Neck.
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Relax on the covered patio with a wooden table and two comfortable chairs.

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

2.0 star property
9.6 out of 10, Exceptional, (5)
"Super, super cute mid-century mod renovated cozy house, walking distance to many things in Colonial Beach. Located just off the main road, this is a great stay. Very comfortable, so beautifully decorated, and great outdoor space. The neighborhood is a little strange because it's a mix of a lot of older homes, located behind a 7-11, BUT it is just a humble area and we felt safe. We were glad to be close to a good coffee shop (Love Bites) and a few restaurants. Easy short walk or drive to the...
The price is NZ$754
includes taxes & fees
20 July - 21 July
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
Discover the charm of Colonial Beach
Guests can enjoy a serene waterfront experience from this tranquil pier.

Discover the charm of Colonial Beach

9.6 out of 10, Exceptional, (5)
"I was in the area for one night for business and had my young granddaughter with me. The room was very comfortable and well furnished. Lots of apps available on the TV. Location is close to plenty of restaurants and the beach. The continental breakfast was very nicely set and had lots of variety. I plan on coming back NOT for business just so I can enjoy another stay. Highly recommend."
The price is NZ$476
includes taxes & fees
17 July - 18 July
Discover the charm of Colonial Beach
4-BR Waterfront Turret Home
Enjoy a comfortable seating area with two rocking chairs and unobstructed views of the surrounding area.

4-BR Waterfront Turret Home

2.0 star property
10.0 out of 10, Exceptional, (4)
"Absolutely wonderful home with the best view of the water from nearly every window. It was clean and it had many comfortable bedrooms. Highly recommend this property!!"
4-BR Waterfront Turret Home
Historic charm with modern amenities
Relax in a shaded patio area surrounded by trees, featuring round tables and comfortable seating under a pergola with climbing plants.

Historic charm with modern amenities

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is NZ$535
includes taxes & fees
17 July - 18 July
Historic charm with modern amenities
High River Bank with $1M Sunset View, 3 min to College
Relax in a serene outdoor space with a bench, swings, and comfortable seating on a patterned floor.

High River Bank with $1M Sunset View, 3 min to College

10.0 out of 10, Exceptional, (1)
"I recently stayed at this property and had a wonderful experience. Trey was a terrific host. The location is fantastic, offering easy access to St. Mary’s College. The water view and sunsets were amazing. The cleanliness of the property was impeccable and the host did a great job of stocking the house with everything we needed. The full kitchen with labeled drawers made cooking easy. The house was roomy and the beds were extremely comfortable. It is a great set up for families. Overall, I highly...
The price is NZ$979
includes taxes & fees
29 July - 30 July
High River Bank with $1M Sunset View, 3 min to College
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Enjoy a serene beach experience with a gentle curve leading into the ocean, adjacent to a tranquil community.

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

10.0 out of 10, Exceptional, (3)
"They thought of everything. I would definitely come back for another stay."
The price is NZ$909
includes taxes & fees
17 July - 18 July
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, a large window, and ample countertop space.

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

9.8 out of 10, Exceptional, (28)
"We loved the waterfront home where we stayed. The host was incredibly helpful and responsive to any questions we had about the rental and the area. Highly recommend."
The price is NZ$1,099
includes taxes & fees
17 July - 18 July
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach
Relax on the spacious deck with a sofa, chairs, and fire pit, surrounded by lush greenery and trees.

Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach

8.8 out of 10, Excellent, (3)
"Tommy and Julya were amazing cleanliness, a great location, the host's hospitality, beautiful decor and amenities, and family-friendly aspects. They emphasize the comfort of the space, the convenience of the location, the attentiveness of the host, amazing experience, I would definitely go back. , beachoverall positive experience. "
The price is NZ$2,712
includes taxes & fees
23 July - 24 July
Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach
18-Acre Waterfront Sanctuary: Peace & Privacy
Escape to a serene lakeside retreat surrounded by dense forest and a tranquil atmosphere.

18-Acre Waterfront Sanctuary: Peace & Privacy

9.6 out of 10, Exceptional, (5)
"Lots to do and very quiet."
The price is NZ$921
includes taxes & fees
17 July - 18 July
18-Acre Waterfront Sanctuary: Peace & Privacy
Game-Themed Water Fun! Boats+Pool+Beach+King Bed
Stroll along the pier, taking in the serene views of the calm water and surrounding landscape.

Game-Themed Water Fun! Boats+Pool+Beach+King Bed

10.0 out of 10, Exceptional, (27)
"Great spot"
The price is NZ$1,050
includes taxes & fees
30 July - 31 July
Game-Themed Water Fun! Boats+Pool+Beach+King Bed
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
Relax in this serene bedroom with a large bed and two nightstands, offering a view of the outdoors through a large window.

Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.

9.4 out of 10, Exceptional, (3)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
The price is NZ$868
includes taxes & fees
21 July - 22 July
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
4-bedroom house in wonderful Colonial Beach
Property grounds

4-bedroom house in wonderful Colonial Beach

The price is NZ$1,103
includes taxes & fees
22 July - 23 July
4-bedroom house in wonderful Colonial Beach
Luxury Modern Waterfront Retreat
Enjoy cooking in this well-equipped kitchen with a large island, stainless steel appliances, and ample counter space.

Luxury Modern Waterfront Retreat

10.0 out of 10, Exceptional, (11)
"The property was ideal for our group and our 4 legged "kids". Lots of space inside and out. We can't wait to go back!"
The price is NZ$1,199
includes taxes & fees
28 July - 29 July
Luxury Modern Waterfront Retreat
Roomy 6 bedroom home in the heart of Solomons, MD
Enjoy cooking in this well-equipped kitchen with a dishwasher, sink, and ample counter space.

Roomy 6 bedroom home in the heart of Solomons, MD

9.2 out of 10, Wonderful, (5)
"Stayed for business, completed our project and enjoyed some local eating spots. "
The price is NZ$1,354
includes taxes & fees
5 Aug - 6 Aug
Roomy 6 bedroom home in the heart of Solomons, MD
Kentigern at Scotland Yards
Situated by the water, this building offers a setting with a spacious balcony overlooking the surrounding trees.

Kentigern at Scotland Yards

9.8 out of 10, Exceptional, (129)
"Great location and nice view"
Kentigern at Scotland Yards
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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Frequently asked questions

Are there holiday rentals in Leonardtown?

Yes, there are holiday rentals in Leonardtown close to Saint Mary's Fairground, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Leonardtown has to offer?

Waterfront 3-Bed Oasis Perfect for City Getaway: This holiday home rental outside of Leonardtown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals will I find in Leonardtown?

With 11 Expedia holiday rentals, you're guaranteed 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 Leonardtown Park are a couple of lovely local spots to get outside and enjoy nature. While here, Port of Leonardtown Winery and Leonardtown Town Hall are other places worth a visit.

What’s a holiday rental in Leonardtown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Leonardtown. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.