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

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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 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 £210
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 £266
includes taxes & fees
20 Oct - 21 Oct
Bright and airy waterfront getaway
Pool

3. 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 £344
includes taxes & fees
27 Oct - 28 Oct
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

4. 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 £224
includes taxes & fees
20 Oct - 21 Oct
The Cozy Crab- Your Charming Haven in Lovely North Beach!
A pathway lined with trees and lights leading to a wooden building with a visible window.

5. 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 £642
includes taxes & fees
20 Oct - 21 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.

6. 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 £729
includes taxes & fees
20 Oct - 21 Oct
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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.

7. 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 £884
includes taxes & fees
20 Oct - 21 Oct
Lakefront Cabin Near Solomons Island w/ Hot Tub
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 £552
includes taxes & fees
20 Oct - 21 Oct
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, (24 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is £249
includes taxes & fees
28 Oct - 29 Oct
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
The price is £341
includes taxes & fees
3 Nov - 4 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A sign for Herrington Harbour with a clear sky and parked cars in the background.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (4 reviews)
"Warm and cozy- amazing home, beautiful area"
United States
Sodbileg
Rose Haven Coastal Cottage
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 £631
includes taxes & fees
26 Oct - 27 Oct
2 Acre Oasis with Private Beach! Family and dog friendly!
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 £189
includes taxes & fees
20 Oct - 21 Oct
Waterfront Getaway with Dock
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

14. 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 £387
includes taxes & fees
21 Oct - 22 Oct
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.

15. 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 £313
includes taxes & fees
20 Oct - 21 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
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 £512
includes taxes & fees
20 Oct - 21 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 £574
includes taxes & fees
30 Oct - 31 Oct
Charming Waterfront 3-bedroom house in Piney Point
A view from a room to a glass door leading outside.

18. 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 £584
includes taxes & fees
2 Nov - 3 Nov
Tranquil Modern Farmhouse
A coastal area with a sandy beach, a clear blue sea, and a small settlement with houses.

19. 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 £357
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.
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Top St. Leonard Hotel Reviews

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

10/10 Excellent
"Enjoyable stay with friendly staff"
David 2-night trip
Posted 3 hours ago
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

Find out more about St. Leonard

St. Leonard Holiday Homes information

Number of reviews
397
Accommodation
242 Holiday Homes
Lowest Price
£189
Highest Price
£884