A beach at sunset with a wooden fence in the background.

Holiday Homes in St. Leonard

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for St. Leonard holiday homes

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

1. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €258
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

2. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A lakeside view with chairs and a table, a rainbow, and trees.

3. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is €320
includes taxes & fees
30 Nov - 1 Dec
Bright and airy waterfront getaway
A pathway lined with trees and lights leading to a wooden building with a visible window.

4. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.6 out of 10, Exceptional, (15 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is €767
includes taxes & fees
2 Nov - 3 Nov
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa and a dining table, and a large window providing natural light.

5. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (2 reviews)
"Very much enjoyed our stay. The host was very kind and responsive and the property very comfortable. Hot tub and quiet location were great!"
United States
Tanya S.
The price is €1,016
includes taxes & fees
1 Nov - 2 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

6. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

7. Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Lusby
10.0 out of 10, Exceptional, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is €871
includes taxes & fees
3 Nov - 4 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A spacious living room with a large sofa, a television, and a view of the ocean.

8. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €659
includes taxes & fees
1 Nov - 2 Nov
4-BR Waterfront Turret Home
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

9. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is €284
includes taxes & fees
1 Nov - 2 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

10. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

11. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
Sunset Breezes - quiet waterfront retreat
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

12. 2 Acre Oasis with Private Beach! Family and dog friendly!

2 Acre Oasis with Private Beach! Family and dog friendly!
Leonardtown
10.0 out of 10, Exceptional, (67 reviews)
"Everything about this property is wonderful for our family! A dreamy relaxing vacation"
United States
Carol L.
The price is €754
includes taxes & fees
2 Nov - 3 Nov
2 Acre Oasis with Private Beach! Family and dog friendly!
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

13. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (17 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is €430
includes taxes & fees
11 Nov - 12 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A covered patio with a view of a lake, furnished with chairs and a table.

14. Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Lexington Park
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is €363
includes taxes & fees
3 Nov - 4 Nov
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

15. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is €215
includes taxes & fees
1 Nov - 2 Nov
Waterfront Getaway with Dock
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

16. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"Overall I had a wonderful stay... however I wish it was booked for a summertime day... the brand new pool looked very appealing & I wish I couldve enjoyed using it. Will have to try & stay again during the summer for a nice pool day!"
United States
Jay W.
The price is €709
includes taxes & fees
16 Nov - 17 Nov
Tranquil Modern Farmhouse
A two-story house with a balcony, surrounded by trees and a wooden fence.

17. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (8 reviews)
"This property was perfect for our night visiting St. Mary's! Spacious, right on the water, and quiet. Thank you!"
United States
Meira
The price is €643
includes taxes & fees
2 Nov - 3 Nov
Charming Waterfront 3-bedroom house in Piney Point
A coastal area with a sandy beach, a clear blue sea, and a small settlement with houses.

18. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is €411
includes taxes & fees
1 Nov - 2 Nov
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"."
Noelle 2-night trip
Posted 10 hours ago
Rod 'N' Reel Resort

Find out more about St. Leonard

St. Leonard Holiday Homes information

Number of reviews
406
Accommodation
242 Holiday Homes
Lowest Price
€215
Highest Price
€1,016