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Leonardtown Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Leonardtown holiday rentals

Property grounds
Potomac Vista Cottage

Holiday Home in Leonardtown

Potomac Vista Cottage
2.0 star property
The price is HK$1,082
HK$3,052 total
includes taxes & fees
19 Jan - 20 Jan
Potomac Vista Cottage
Fridge, microwave, oven, stovetop
Anne & Fred`s Leonardtown Home W/ Arcade room!

Apartment in Leonardtown

Anne & Fred`s Leonardtown Home W/ Arcade room!
9.2 out of 10, Wonderful, (5)
"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."
United States
Lauren A.
The price is HK$1,947
HK$4,510 total
includes taxes & fees
12 Jan - 13 Jan
Anne & Fred`s Leonardtown Home W/ Arcade room!
Exterior
Cheery, Peaceful Water Front Cabin on Winery Grounds

Cabin in Colonial Beach

Cheery, Peaceful Water Front Cabin on Winery Grounds
9.8 out of 10, Exceptional, (57)
"Very quiet and great location."
United States
Cindy B.
The price is HK$568
HK$1,635 total
includes taxes & fees
14 Jan - 15 Jan
Cheery, Peaceful Water Front Cabin on Winery Grounds
Exterior
Soul Oasis - home on the Chesapeake Bay

Cottage in Lusby

Soul Oasis - home on the Chesapeake Bay
9.8 out of 10, Exceptional, (40)
"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."
United States
Samuel W.
The price is HK$973
HK$2,113 total
includes taxes & fees
11 Jan - 12 Jan
Soul Oasis - home on the Chesapeake Bay
Fridge, microwave, oven, stovetop
Waterfront home where you can relax or enjoy the things the Northern Neck.

Holiday Home in Lottsburg

Waterfront home where you can relax or enjoy the things the Northern Neck.
10.0 out of 10, Exceptional, (11)
"Property was very nice! Very clean and I especially loved the dual coffee maker!"
United States
Tamara G.
The price is HK$1,168
HK$2,122 total
includes taxes & fees
13 Jan - 14 Jan
Waterfront home where you can relax or enjoy the things the Northern Neck.
Property grounds
Sail Away

Apartment in Colonial Beach

Sail Away
9.8 out of 10, Exceptional, (9)
"Stay was wonderful!"
United States
Karen H.
The price is HK$919
HK$2,256 total
includes taxes & fees
12 Jan - 13 Jan
Sail Away
Dining
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cottage in Point Lookout

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
9.4 out of 10, Exceptional, (10)
"The cottage was clean and welcoming. The location can't be beat. It is right on the water, quiet and nearby point lookout. Great place to visit and walk our dogs. The property owners were responsive and gave us a nice list of things to do around the area. Would definitely stay again!"
United States
Adam P.
The price is HK$1,002
HK$2,457 total
includes taxes & fees
11 Jan - 12 Jan
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Exterior
Coles Point Marina

Cabin in Hague

Coles Point Marina
2.0 star property
The price is HK$2,073
HK$2,918 total
includes taxes & fees
17 Jan - 18 Jan
Coles Point Marina
Marina
Back Creek Villa Open Deck Solomons Island Maryland

Holiday Home in Solomons

Back Creek Villa Open Deck Solomons Island Maryland
2.0 star property
The price is HK$934
HK$2,022 total
includes taxes & fees
10 Jan - 11 Jan
Back Creek Villa Open Deck Solomons Island Maryland
Beach
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach

Cottage in Colonial Beach

Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
9.8 out of 10, Exceptional, (15)
"We love going to Colonial Beach. This house offered everything we were looking for in a mini vacation."
United States
Anonymous traveller
The price is HK$1,830
HK$3,518 total
includes taxes & fees
12 Jan - 13 Jan
Charming 4-bedroom, 2-bath cottage, dog friendly, AC, WiFi, 1 block to beach
Fridge, microwave, oven, stovetop
Luxury Modern Waterfront Retreat

Holiday Home in Montross

Luxury Modern Waterfront Retreat
9.6 out of 10, Exceptional, (14)
"Very nice inside, love all the windows"
United States
Elizabeth S.
The price is HK$873
HK$3,145 total
includes taxes & fees
12 Jan - 13 Jan
Luxury Modern Waterfront Retreat
Smart TV, books
4-BR Waterfront Turret Home

Holiday Home in Solomons

4-BR Waterfront Turret Home
2.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is HK$2,725
HK$5,598 total
includes taxes & fees
21 Jan - 22 Jan
4-BR Waterfront Turret Home
Property grounds
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Cottage in Benedict

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.0 out of 10, Wonderful, (8)
"The owner was very nice "
United States
karen
The price is HK$1,401
HK$2,330 total
includes taxes & fees
21 Jan - 22 Jan
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Sun-loungers
Cottage Located on the Patuxent River!

Cottage in Prince Frederick

Cottage Located on the Patuxent River!
10.0 out of 10, Exceptional, (42)
"This place was very lovely. Beautiful atmosphere and very spacious cottage. Didn’t get to see the owners but really enjoyed their property. Loved having the coffee maker, comfy bed and awesome tub! I will definitely be back. "
United States
RACHEL S.
The price is HK$2,067
HK$2,472 total
includes taxes & fees
16 Jan - 17 Jan
Cottage Located on the Patuxent River!
TV, books, stereo
River Refresh - Waterfront with Spa on Placid Bay

Holiday Home in Colonial Beach

River Refresh - Waterfront with Spa on Placid Bay
10.0 out of 10, Exceptional, (20)
"Fantastic amenities, beautiful view, cosy yet spacious!"
United States
Aaron M.
The price is HK$1,947
HK$4,058 total
includes taxes & fees
12 Jan - 13 Jan
River Refresh - Waterfront with Spa on Placid Bay
Sun-loungers, beach towels
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK

Holiday Home in Montross

Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
10.0 out of 10, Exceptional, (5)
"We enjoyed this house fully for our Thanksgiving stay! We even took the canoes out for a spin. Nice walks around the development and the beach area is lovely. "
United States
Julie I.
The price is HK$1,296
HK$3,172 total
includes taxes & fees
13 Jan - 14 Jan
Modern Waterfront Home with Kayak, Firepit, Gameroom, Pool+Beaches, Dog & EV OK
Interior
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!

Cottage in Lusby

Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
3.0 star property
The price is HK$2,850
HK$6,520 total
includes taxes & fees
19 Jan - 20 Jan
Lakefront Log Cabin Retreat w/ Hot tub + Kayaks!
Exterior
Charming Waterfront 3-bedroom house in Piney Point

Holiday Home in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
10.0 out of 10, Exceptional, (1)
"Beautiful newly renovated space with all new appliances, furniture and kitchenware. Comfortable beds, and super clean rooms. Large outside area with new Weber grill, fire pit, and three kayaks. Nice easy to access dock. "
United States
Kit C.
The price is HK$2,336
HK$4,462 total
includes taxes & fees
10 Jan - 11 Jan
Charming Waterfront 3-bedroom house in Piney Point
Interior
MLK Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar

Holiday Home in Montross

MLK Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
10.0 out of 10, Exceptional, (30)
"Great spot"
United States
SHAWN W.
The price is HK$1,557
HK$3,593 total
includes taxes & fees
11 Jan - 12 Jan
MLK Sale! Game Theme+Boats+King Bd+EV Chrgr+Solar
Smart TV, books
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Holiday Home in Prince Frederick

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
9.6 out of 10, Exceptional, (5)
"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. "
United States
Carrie K.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
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

Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

10/10 Excellent
"Nice updating. Very nice people working on Christmas. "
JOHN 3-night trip
Posted 1 day ago
Solomons Inn Resort & Marina

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 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?

Coastal Charm and Convenience: Luxurious 5-Bedroom Just Steps From Downtown: This holiday home rental outside of Leonardtown is on a river, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Indian Village Archeological Park are a couple of lovely local spots to get outside and enjoy nature. While here, Leonardtown Town Hall and Breton Bay Golf Course 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.