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Vacation rentals in Leonardtown

Vacation rentals in Leonardtown

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Leonardtown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Sandy Beach on Breton Bay with Beach
SUPERHOSTEntire house · 6 guests · 4 beds · 1 bath
Sandy Beach on Breton Bay with Beach

Amazing waterviews, small sandy beach Fish or Crab from sea wall and beachside patio. Quiet serene location, partially privacy fenced, 7 miles from Leonardtown town center. Historic St Clements Island is within view, kayak to the state park on provided kayaks! Enjoy nature while relaxing in the beautifully designed outdoor space, where bald eagles and blue herons are common sightings. Large screen WiFi TV with cable & premium channels., Great amenities here!!! Well mannered pets welcome :)

What guests are saying:

“Ruth's place gave us a much-needed break from DC. We spent a wonderful long weekend listening to the waves and sitting in the backyard. Our dog loved the fenced-in yard and playing in the sand on the beach. The kitchen is really well stocked and the rooms are quiet and comfortable. I can't recommend this location enough and hope to come back soon!”

Adorable Waterfront Apartment Weekend Getaway
SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

What guests are saying:

“For the better part of the last ten years my wife & I have celebrated our June anniversary somewhere on Maryland water. This year for our 31st anniversary I chose St. Mary’s as our destination. We both love history, being around water and other outdoor activities; hiking, biking and kayaking. After reading the reviews of this apartment I booked it, only hoping things were as described and shown in the pictures. Well, we were not disappointed, as this is simply a spectacular setting on the banks of the St. Mary’s River, with a view across the cape of St. Mary’s College. Everything was as described, and in person it was even better; the beautiful decoration and design of the apartment, the spacious kitchen, living room, bedroom and bathroom, not to mention the many personal touches and extra amenities. Theresa was in constant touch, providing us with ideas for dining, detailed directions to the apartment, and even going out of her way to purchase perhaps the most delicious muffins ever for our first breakfast. The space out on the boat dock was simply perfect, whether we used it during the day for reading, protected from the sun by the shade sails or enjoying a few glasses of wine at night in the glow of the mini string lights, creating the PERFECT ambience to relax after a day of sightseeing. Our trip didn’t end without Theresa providing one more suggestion - traveling through Solomon’s Island and stopping by Lotus Kitchen for a breakfast croissant and delicious Key Lime pie! It really was the most perfect stay - thank you!”

Home away from home
SUPERHOSTPrivate room · 1 guest · 1 bed · 1 shared bath
Home away from home

1 bedroom with shared bathroom only if another guest is present. Separate family room with TV, microwave and refridgerator shared between the 2 bedrooms. Direct TV and free WiFi for guests. Walking to nearby hospital and nursing home convenient for traveling nurse or physical therapist. Close to Pax River Naval base and Calvert Cliffs power plant. Space is cozy and comfortable

What guests are saying:

“This was an amazing experience, especially for my first time in South Maryland. Would 100% visit again because of how hospitable and kind Kim was. Also very affordable. The overall area was very beautiful and private! I had an awesome stay!”

Holiday rentals for every style

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Popular amenities for Leonardtown holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Leonardtown

Historic St.Mary's City at the Lazy Bear Cottage
SUPERHOSTTiny house
Historic St.Mary's City at the Lazy Bear Cottage
Price:$97 AUD / night
The Underground
SUPERHOSTPrivate room
The Underground
Price:$51 AUD / night
Private cabana on a pier!
SUPERHOSTTiny house
Private cabana on a pier!
Price:$211 AUD / night
Gettin to the point. ( Cove Point Beach)
SUPERHOSTEntire cottage
Gettin to the point. ( Cove Point Beach)
Price:$169 AUD / night
Downtown Retreat With Water Views!
SUPERHOSTEntire house
Downtown Retreat With Water Views!
Price:$246 AUD / night
Tranquil River Home
SUPERHOSTEntire house
Tranquil River Home
Price:$155 AUD / night
PRIVATE BR + OFFICE/LV RM NEAR NAS PAX SHARED HSE
SUPERHOSTPrivate room
PRIVATE BR + OFFICE/LV RM NEAR NAS PAX SHARED HSE
Price:$54 AUD / night
Riverfront Chalet
Kayak, canoe or pier, breakfast!
SUPERHOSTEntire guest suite
Riverfront Chalet Kayak, canoe or pier, breakfast!
Price:$158 AUD / night
Charming 1930s Farmhouse on Scenic Farm
SUPERHOSTEntire house
Charming 1930s Farmhouse on Scenic Farm
Price:$180 AUD / night
Creek Side Loft: Hospitality is Our Gift to You
SUPERHOSTEntire loft
Creek Side Loft: Hospitality is Our Gift to You
Price:$140 AUD / night
New Private Living Space In Great Location!
Entire apartment
New Private Living Space In Great Location!
Price:$57 AUD / night
Our Little Piece of Heaven
SUPERHOSTEntire apartment
Our Little Piece of Heaven
Price:$176 AUD / night
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