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Check prices for these dates

Next weekend
Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select St. Leonard Cabin Rentals

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Relax on the deck with ocean views, featuring a table and chairs.

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (177)
"The views are fantastic. Very quiet neighborhood. "
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Maryland Vacation Rental w/ Private Pool & Dock
Enjoy meals al fresco on this deck surrounded by lush greenery.

Maryland Vacation Rental w/ Private Pool & Dock

9.2 out of 10, Wonderful, (12)
"Had a great time fishing from the dock while we got out of the city for a weekend."
Maryland Vacation Rental w/ Private Pool & Dock
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Relax in a spacious room with a comfortable seating area, sofa, and large windows offering a view of the outdoors.

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

9.8 out of 10, Exceptional, (7)
"Lovely property right on the water. Very peaceful and perfect for a short getaway! We enjoyed using the fire pit on the last evening of our stay. Great family memories!"
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
El Camino
Relax on the deck with two comfortable chairs, surrounded by trees and shrubs in a serene wooded environment.

El Camino

10.0 out of 10, Exceptional, (43)
"Awesome location and accommodations. Very clean and comfortable. "
El Camino
Pizza Friday
Built into a rustic cabin, this outdoor oven features three brick arches for wood storage.

Pizza Friday

10.0 out of 10, Exceptional, (8)
"Perfect location for our stay in the area. Everything about the property is quite generous. Will stay here again and again."
Pizza Friday
Vintage Waterfront A Frame- Hideaway On The Bay
Situated in a wooded area, this cabin-style building features a front porch and a small deck leading to the entrance.

Vintage Waterfront A Frame- Hideaway On The Bay

10.0 out of 10, Exceptional, (4)
"We had a lovely few days away for Spring Break, home was perfect for family of 4 who loves some quiet time and time to be outside! Thanks for hosting us!"
Vintage Waterfront A Frame- Hideaway On The Bay
Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Relax in a serene outdoor setting with a hot tub surrounded by lounge chairs and a wooden dock.

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

10.0 out of 10, Exceptional, (18)
"Was beautiful and very relaxing!"
Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade
Waterfront cabin with incredible sunsets on Maryland's Eastern Shore.
Situated on a grassy area, this charming home features a front porch with a bench and a small entryway.

Waterfront cabin with incredible sunsets on Maryland's Eastern Shore.

Waterfront cabin with incredible sunsets on Maryland's Eastern Shore.
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 St. Leonard Hotel Reviews

The Inn at Leonardtown, Ascend Hotel Collection

The Inn at Leonardtown, Ascend Hotel Collection

10/10 Excellent
"Staff was very friendly, room was clean. "
Shawn 2-night trip
Posted 21 hours ago
The Inn at Leonardtown, Ascend Hotel Collection