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

Search Vacation Homes in St. Leonard

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for St. Leonard vacation 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 AED 499
AED 1,016 total
includes taxes & fees
26 Oct - 27 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A lakeside view with chairs and a table, a rainbow, and trees.

2. 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 AED 845
AED 1,406 total
includes taxes & fees
25 Oct - 26 Oct
Bright and airy waterfront getaway
A pathway lined with trees and lights leading to a wooden building with a visible window.

3. 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 traveler
The price is AED 1,697
AED 3,134 total
includes taxes & fees
21 Oct - 22 Oct
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.

4. 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 AED 1,708
AED 4,279 total
includes taxes & fees
26 Oct - 27 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

5. 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, (3 reviews)
"We loved the quiet location, the privacy, and the dock out back. The house was stocked with everything we needed!"
United States
Nicholas L.
The price is AED 1,293
AED 3,554 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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 price is AED 437
AED 1,086 total
includes taxes & fees
16 Nov - 17 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A spacious living room with a large sofa, a television, and a view of the ocean.

7. 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 AED 1,102
AED 2,573 total
includes taxes & fees
21 Oct - 22 Oct
4-BR Waterfront Turret Home
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

8. 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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AED 453
AED 1,356 total
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.

9. 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
The price is AED 518
AED 1,657 total
includes taxes & fees
25 Oct - 26 Oct
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.

10. 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.
The price is AED 948
AED 1,180 total
includes taxes & fees
17 Nov - 18 Nov
Sunset Breezes - quiet waterfront retreat
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

11. 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 AED 1,455
AED 3,109 total
includes taxes & fees
26 Oct - 27 Oct
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.

12. 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 AED 905
AED 1,882 total
includes taxes & fees
27 Oct - 28 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

13. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AED 760
AED 923 total
includes taxes & fees
25 Oct - 26 Oct
Waterfront Getaway with Dock
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 AED 735
AED 1,501 total
includes taxes & fees
27 Oct - 28 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

15. 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 AED 1,567
AED 2,866 total
includes taxes & fees
2 Nov - 3 Nov
Tranquil Modern Farmhouse
A spacious living room with a large TV, blue sofa, and a ceiling fan.

16. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"
United States
Joyce F.
The price is AED 1,312
AED 2,481 total
includes taxes & fees
21 Oct - 22 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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, (7 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 AED 1,131
AED 2,763 total
includes taxes & fees
30 Oct - 31 Oct
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, Dock+Kayak, Firepit, Game room, Potomac 2hrs to DC, Dogs+EV OK

Waterfront, Dock+Kayak, Firepit, Game room, Potomac 2hrs to DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AED 642
AED 1,742 total
includes taxes & fees
26 Oct - 27 Oct
Waterfront, Dock+Kayak, Firepit, Game room, Potomac 2hrs to DC, Dogs+EV OK
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top St. Leonard Hotel Reviews

Sleep Inn & Suites California MD

Sleep Inn & Suites California MD

8/10 Good
"Very clean"
Jackie 1-night trip
Posted 3 hours ago
Sleep Inn & Suites California MD