St. Leonard Vacation Rentals

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Check prices for these dates

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

Browse Select St. Leonard Vacation Homes

Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Relax in this spacious living area with a large sofa, dining table, and ceiling fan.

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

10.0 out of 10, Exceptional, (49)
"Awesome home wnd location! Would stay again!"
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Rising Sun Bay View Cottage
Relax in a serene outdoor space with a bench, table, and rocking chair, surrounded by a playground and lush views.

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Enjoy a serene view of the water from this deck, surrounded by lush greenery and a comfortable seating area.

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

9.8 out of 10, Exceptional, (44)
"Beautiful views and a lush backyard. Jacob was excellent with communication. The house was clean and had all amenities needed for a wonderful stay. Please note there are a lot of stairs in the house as well as get to the dock. It was a good workout for us!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (129)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
The Blue Crab Beach House - Free beach passes
Relax on the beach with a serene view of the ocean from the pier's benches and gazebo.

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (66)
"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."
The Blue Crab Beach House - Free beach passes
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Stroll along the pier, taking in the serene coastal views and tranquil atmosphere.

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (120)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront Wildlife Retreat on the Patuxent River
Enjoy expansive views of the surrounding landscape from the high ceiling and large windows.

Waterfront Wildlife Retreat on the Patuxent River

10.0 out of 10, Exceptional, (167)
"The Waterfront Retreat on the Patuxent River is better than advertised. Our whole family stayed -- everyone loved it! It was clean, comfortable, with everything needed to stay comfortably, sleep, eat, relax and use as a home base for exploring. Solomons Island and the surrounding area was filled with lots of fun things to do (restaurant's, museums, history, boating, walking, etc.). "
Waterfront Wildlife Retreat on the Patuxent River
Beautiful Waterfront Retreat in Cambridge!
Relax in this cozy room with a bar area featuring a large window offering a view of the outdoors.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (42)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $353
CA $677 total
includes taxes & fees
Aug 12 - Aug 13
Beautiful Waterfront Retreat in Cambridge!
WATERFRONT!!! The River's Roost on The Patuxent River
Enjoy cooking in this well-equipped kitchen with a gas range, oven, and ample counter space.

WATERFRONT!!! The River's Roost on The Patuxent River

10.0 out of 10, Exceptional, (25)
"Great stay, beautiful spot. We will be back for sure."
WATERFRONT!!! The River's Roost on The Patuxent River
Waterfront 3-Bedroom Cottage and Pet Friendly
Enjoy a meal or drink with a view of the sea from this dining area.

Waterfront 3-Bedroom Cottage and Pet Friendly

10.0 out of 10, Exceptional, (32)
"This beautiful home was wonderful for our long overdue vacation - We loved our stay here very much - The town is amazing "
Waterfront 3-Bedroom Cottage and Pet Friendly
Hoopers Island Retreat
WiFi, bed sheets

Hoopers Island Retreat

Hoopers Island Retreat
Bright and airy waterfront getaway
Escape to a serene lakeside haven with a wide sandy beach and tranquil water views.

Bright and airy waterfront getaway

9.8 out of 10, Exceptional, (16)
"This property was everything we wanted. We hope to return next year."
Bright and airy waterfront getaway
Screened Patio, Deck & Grill: Saint Inigoes Home!
Enjoy al fresco dining with a view of the surrounding landscape from this outdoor space featuring a table and chairs.

Screened Patio, Deck & Grill: Saint Inigoes Home!

9.6 out of 10, Exceptional, (7)
"great location relative to smc for a campus visit"
Screened Patio, Deck & Grill: Saint Inigoes Home!
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
Relax on the waterfront with lounge chairs and a wooden pier.

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

10.0 out of 10, Exceptional, (15)
"Place was beautiful and peaceful. Great place for a quiet getaway! Owners were very accommodating and helpful."
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
The Lazy Crab Beach House - Free beach passes
Welcome to The Lazy Cat North Beach, featuring a charming front porch with a potted plant and a decorative welcome sign.

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (54)
"Great stay"
The Lazy Crab Beach House - Free beach passes
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Relax by the pool with a seating area and grill, perfect for outdoor dining or cooking.

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (8)
"My husband and I spent Christmas on Tilghman Island in this unique house right on the water. It was perfect for us to rest, relax and cook Christmas dinner. We enjoyed it so much we want to visit again when the boats are out. The yard was perfect for our dog to get some exercise. I can see this as a perfect place for family and friends in the summer."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Discover tranquility near Calvert Cliffs
Relax on the lakeside deck with a table and four chairs, surrounded by lush greenery and a serene atmosphere.

Discover tranquility near Calvert Cliffs

9.8 out of 10, Exceptional, (16)
"Comfortable beds, large house with awesome views…had a great experience"
Discover tranquility near Calvert Cliffs
Walk to Beach: Elegant Escape in Lusby!
Enjoy cooking in this well-equipped kitchen with a dining table for four, oven, microwave, coffee maker, and toaster.

Walk to Beach: Elegant Escape in Lusby!

10.0 out of 10, Exceptional, (1)
"The property was very comfortable, convenient, well organized and beautifully prepared. "
Walk to Beach: Elegant Escape in Lusby!
Stunning secluded Luxury waterfront cottage with private deep water pier!
Surrounded by a serene forest, this two-story retreat offers a cozy balcony and a peaceful ambiance.

Stunning secluded Luxury waterfront cottage with private deep water pier!

10.0 out of 10, Exceptional, (79)
"This property was exactly as described. The owner was very easy to work with. Unfortunately, we did not get to use the fire pit as it was rainy and cold. I would 100% stay here again."
Stunning secluded Luxury waterfront cottage with private deep water pier!
Private Waterfront Home with Dock in Solomons, MD
Kitchen features a white gas stove, microwave, and sink with a black countertop, complemented by a patterned rug and white cabinetry.

Private Waterfront Home with Dock in Solomons, MD

10.0 out of 10, Exceptional, (6)
"Nice and cozy"
Private Waterfront Home with Dock in Solomons, MD
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 1 day ago
The Inn at Leonardtown, Ascend Hotel Collection