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

Holiday 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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 NZ$446
includes taxes & fees
30 Sept - 1 Oct
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is NZ$806
includes taxes & fees
20 Oct - 21 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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, (24 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 NZ$609
includes taxes & fees
24 Sept - 25 Sept
Bright and airy waterfront getaway
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

4. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is NZ$801
includes taxes & fees
24 Sept - 25 Sept
Plum Point Cottage #17
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

5. 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, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is NZ$587
includes taxes & fees
27 Sept - 28 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A spacious cabin interior with a wooden ceiling, a kitchen area, a living room with a sofa, and a dining table.

6. 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 NZ$2,023
includes taxes & fees
24 Sept - 25 Sept
Lakefront Cabin Near Solomons Island w/ Hot Tub
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, (12 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is NZ$1,253
includes taxes & fees
4 Oct - 5 Oct
4-BR Waterfront Turret Home
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

8. 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, (37 reviews)
"We enjoyed our stay in North Beach at this lovely residence. It was spacious, clean, nicely furnished and only a few minutes walk to the bay. The beds were so comfortable too!!"
United States
Penny N.
The price is NZ$782
includes taxes & fees
29 Sept - 30 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A pathway lined with trees and lights leading to a wooden building with a visible window.

9. 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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
The price is NZ$1,456
includes taxes & fees
7 Oct - 8 Oct
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

10. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is NZ$1,720
includes taxes & fees
20 Oct - 21 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
"Great place to stay! Location was nice and close to water views. House was charming and CLEAN. Owners went above and beyond to make the stay welcoming and convenient. Price was reasonable until additional Vrbo fees were added."
United States
Sharon t.
The price is NZ$772
includes taxes & fees
29 Sept - 30 Sept
Rose Haven Coastal Cottage
A covered patio with a view of a lake, furnished with chairs and a table.

12. 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, (16 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is NZ$666
includes taxes & fees
28 Sept - 29 Sept
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.

13. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is NZ$431
includes taxes & fees
4 Oct - 5 Oct
Waterfront Getaway with Dock
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

14. 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 NZ$846
includes taxes & fees
27 Sept - 28 Sept
Sunset Breezes - quiet waterfront retreat
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

15. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is NZ$1,106
includes taxes & fees
6 Oct - 7 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A coastal area with a sandy beach, a small settlement, and a clear view of the sea.

16. Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr 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 NZ$815
includes taxes & fees
28 Sept - 29 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
A spacious living room with a large TV, blue sofa, and a ceiling fan.

17. 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)
"Great house for a large group! Very well equipped kitchen and comfortable home. Extra pillows and black out curtains would be the only thing I would add."
United States
Ximena G.
The price is NZ$1,230
includes taxes & fees
5 Oct - 6 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A modern kitchen with granite countertops, stainless steel appliances, and large windows offering views of the outdoors.

18. 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, (65 reviews)
"Beautiful location "
United States
Jonathan M.
The price is NZ$1,421
includes taxes & fees
7 Oct - 8 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!
A two-story house with a balcony, surrounded by trees and a wooden fence.

19. 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 NZ$1,266
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point
A lakeside property with a large house, a shed, and a dense forest in the background.

20. 'The Bayside Escape' Remote Chesapeake Bay Estate

'The Bayside Escape' Remote Chesapeake Bay Estate
Fishing Creek
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved our stay. They house was beautiful, the amenities were excellent, and we loved the crabs!! We went for a family weekend (mix of 18 kids and adults) and it was very spacious and comfortable for everyone. The pergola in the back was an especially big hit! We highly recommend and would stay again."
United States
Bridget C.
'The Bayside Escape' Remote Chesapeake Bay Estate
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

10/10 Excellent
"Staff was very welcoming and room was clean."
Thomas 1-night trip
Posted 6 hours ago
Sleep Inn & Suites California MD

Find out more about St. Leonard

St. Leonard Holiday Homes information

Number of reviews
283
Accommodation
243 Holiday Homes
Lowest Price
NZ$446
Highest Price
NZ$2,023