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Leonardtown Holiday Rentals

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Check prices for these dates

Tonight
18 Jul - 19 Jul
Tomorrow
19 Jul - 20 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 HK$1,962
HK$4,330 total
includes taxes & fees
22 Jul - 23 Jul
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 HK$1,095
HK$1,943 total
includes taxes & fees
29 Jul - 30 Jul
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, (15)
"Wonderful getaway! "
The price is HK$1,962
HK$4,107 total
includes taxes & fees
18 Aug - 19 Aug
River Refresh - Waterfront with Spa on Placid Bay
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 HK$808
HK$2,612 total
includes taxes & fees
20 Jul - 21 Jul
7 mins to the beach! Fire Pit, BBQ, Games, Fully Equipped Kitchen & Beach Gear
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 HK$1,374
HK$2,316 total
includes taxes & fees
18 Aug - 19 Aug
Waterfront home where you can relax or enjoy the things the Northern Neck.
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 HK$1,261
HK$3,535 total
includes taxes & fees
21 Jul - 22 Jul
Riverside Dreams -golfcart-views-screened porch-
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!!"
The price is HK$3,532
HK$6,905 total
includes taxes & fees
23 Jul - 24 Jul
4-BR Waterfront Turret Home
Historic charm with modern amenities
Enjoy a day of swimming and playing in the calm waters, surrounded by beach chairs and shaded areas under the trees.

Historic charm with modern amenities

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is HK$2,157
HK$2,489 total
includes taxes & fees
21 Jul - 22 Jul
Historic charm with modern amenities
Discover the charm of Colonial Beach
Relax on the beach with calm waters and scenic views, perfect for swimming, sunbathing, and leisure activities.

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 HK$1,780
HK$2,216 total
includes taxes & fees
21 Jul - 22 Jul
Discover the charm of Colonial Beach
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 HK$7,978
HK$12,658 total
includes taxes & fees
23 Jul - 24 Jul
Family Luxury: 5BR, GameRm, MovieRm, Kayaks, PingPong, Fire Pit, Beach
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, (2)
"This was our second time staying at this beautiful home, and it was just as wonderful as we remembered. The house is impeccably maintained, tastefully decorated, and incredibly comfortable. The beds are cozy, and every detail has been thoughtfully considered—from the clear labels throughout the home to the fully stocked kitchen and amenities. It truly feels like a home away from home. We had a fantastic stay and are already looking forward to our next visit!"
The price is HK$1,837
HK$3,604 total
includes taxes & fees
22 Jul - 23 Jul
High River Bank with $1M Sunset View, 3 min to College
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 HK$1,887
HK$5,128 total
includes taxes & fees
18 Aug - 19 Aug
Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit! AMAZING Sweeping VIEWS!
4-bedroom house in wonderful Colonial Beach
Microwave, oven, stovetop, dishwasher

4-bedroom house in wonderful Colonial Beach

The price is HK$2,865
HK$5,678 total
includes taxes & fees
18 Aug - 19 Aug
4-bedroom house in wonderful Colonial Beach
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 HK$2,355
HK$3,985 total
includes taxes & fees
21 Jul - 22 Jul
Kick back and enjoy the Chesapeake & this 3-bedroom, calm, stylish space.
Game-Themed Water Fun! Boats+Pool+Beach+King Bed
Enjoy a serene view of the water and a tree from this room's large window, accompanied by comfortable seating and a convenient bookshelf.

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

10.0 out of 10, Exceptional, (27)
"Great spot"
The price is HK$2,668
HK$4,918 total
includes taxes & fees
30 Jul - 31 Jul
Game-Themed Water Fun! Boats+Pool+Beach+King Bed
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 HK$2,433
HK$5,158 total
includes taxes & fees
28 Jul - 29 Jul
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 HK$3,249
HK$5,782 total
includes taxes & fees
18 Aug - 19 Aug
Roomy 6 bedroom home in the heart of Solomons, MD
Kentigern at Scotland Yards
Enjoy a serene view of the water and forest from the comfort of this stylish room, featuring a sofa and unique ceiling design.

Kentigern at Scotland Yards

9.8 out of 10, Exceptional, (129)
"Great location and nice view"
The price is HK$5,102
HK$9,101 total
includes taxes & fees
25 Jul - 26 Jul
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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Top Leonardtown Hotel Reviews

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick

10/10 Excellent
"Was clean haven't been in ibe as ckean as that fir a long time. Staff was friendly and helpful will definitely be back "
Pamela 1-night trip
Posted 2 days ago
SureStay by Best Western Prince Frederick

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.