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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 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, 8, (8 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is €229
includes taxes & fees
23 Sept - 24 Sept
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, 7, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is €387
includes taxes & fees
16 Sept - 17 Sept
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, 24, (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 €309
includes taxes & fees
16 Sept - 17 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 €406
includes taxes & fees
16 Sept - 17 Sept
Plum Point Cottage #17

5. 3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace

3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
Lusby
The price is €340
includes taxes & fees
12 Oct - 13 Oct
3-bedroom house in serene Lusby with refreshing AC, heat, outdoor fireplace
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

6. 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, 37, (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 €328
includes taxes & fees
16 Sept - 17 Sept
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A spacious cabin with a wooden interior, a fireplace, a television, and a dining area.

7. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, 2, (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 €994
includes taxes & fees
12 Oct - 13 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, 10, (10 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is €598
includes taxes & fees
21 Sept - 22 Sept
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, 23, (23 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is €348
includes taxes & fees
28 Sept - 29 Sept
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A pathway lined with trees and lights leading to a wooden building with a visible window.

10. 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, 14, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveller
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

11. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, 66, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is €239
includes taxes & fees
4 Oct - 5 Oct
Waterfront Getaway with Dock
A cozy living room with a large sectional sofa, a round woven coffee table, and a ceiling fan.

12. 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, 2, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is €990
includes taxes & fees
27 Sept - 28 Sept
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
A covered patio with a view of a lake, furnished with chairs and a table.

13. 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, 16, (16 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is €334
includes taxes & fees
28 Sept - 29 Sept
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
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, 45, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is €424
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, 16, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is €530
includes taxes & fees
29 Sept - 30 Sept
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A laundry room with a washing machine and dryer, wooden cabinets above, and a shelf with a bottle.

16. 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 €422
includes taxes & fees
16 Sept - 17 Sept
Rose Haven Coastal Cottage
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, 35, (35 reviews)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is €646
includes taxes & fees
21 Sept - 22 Sept
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
An aerial view of a coastal area with a sandy beach, a small settlement with houses, and a calm sea.

18. 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, 5, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is €411
includes taxes & fees
16 Sept - 17 Sept
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
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, 7, (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 €685
includes taxes & fees
22 Sept - 23 Sept
Charming Waterfront 3-bedroom house in Piney Point
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

20. Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, 10, (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 €658
includes taxes & fees
21 Sept - 22 Sept
Tranquil Modern Farmhouse
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 Tilghman Island Inn

The Tilghman Island Inn

10/10 Excellent
"Clean. Friendly. Beautiful grounds."
Jeffrey 1-night trip
Posted 3 hours ago
The Tilghman Island Inn

Find out more about St. Leonard

St. Leonard Holiday Homes information

Number of reviews
224
Accommodation
242 Holiday Homes
Lowest Price
€229
Highest Price
€994