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

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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 459
AED 978 total
includes taxes & fees
19 Oct - 20 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 760
AED 1,304 total
includes taxes & fees
8 Oct - 9 Oct
Bright and airy waterfront getaway
Pool

3. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 AED 529
AED 1,659 total
includes taxes & fees
8 Oct - 9 Oct
Family Beach House: Spacious Deck, Grill & Views
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 AED 1,001
AED 1,681 total
includes taxes & fees
21 Oct - 22 Oct
Plum Point Cottage #17
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 traveler
The price is AED 1,697
AED 3,126 total
includes taxes & fees
8 Oct - 9 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.

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.
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.

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, (3 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is AED 1,767
AED 3,528 total
includes taxes & fees
7 Nov - 8 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
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 375
AED 1,282 total
includes taxes & fees
3 Nov - 4 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A spacious living room with a large sofa, a television, and a view of the ocean.

9. 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.
4-BR Waterfront Turret Home
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, (38 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 AED 503
AED 1,613 total
includes taxes & fees
12 Oct - 13 Oct
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A bunk bed with a wooden frame, white bedding, and a blue pillow with a floral design.

11. Rose Haven Coastal Cottage

Rose Haven Coastal Cottage
North Beach
10.0 out of 10, Exceptional, (1 review)
"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 AED 826
AED 1,591 total
includes taxes & fees
18 Oct - 19 Oct
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, (66 reviews)
"Beautiful location "
United States
Jonathan M.
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.

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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AED 1,338
AED 2,419 total
includes taxes & fees
19 Oct - 20 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.

14. 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 892 total
includes taxes & fees
18 Oct - 19 Oct
Waterfront Getaway with Dock
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, (17 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AED 735
AED 1,501 total
includes taxes & fees
20 Oct - 21 Oct
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
A two-story house with a balcony, surrounded by trees and a wooden fence.

16. 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 2,809 total
includes taxes & fees
19 Oct - 20 Oct
Charming Waterfront 3-bedroom house in Piney Point
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)
"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 1,322
AED 2,492 total
includes taxes & fees
13 Oct - 14 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A modern living room with a grey sofa, a dining table with chairs, and large windows with autumn foliage views.

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 AED 1,547
AED 2,840 total
includes taxes & fees
19 Oct - 20 Oct
Tranquil Modern Farmhouse
A coastal area with a sandy beach, a small settlement, and a clear view of the sea.

19. Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from DC, Dogs+EV OK

Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from 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 603
AED 1,684 total
includes taxes & fees
8 Oct - 9 Oct
Waterfront, Firepit, Kayak, Game room, Potomac 2hrs from 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

Island Inn & Suites, an Ascend Collection Hotel

Island Inn & Suites, an Ascend Collection Hotel

10/10 Excellent
"Nice staff and clean and quiet hotel. Literally right on the water in a fairly remote location. Highly recommended."
Michael 1-night trip
Posted 9 hours ago
Island Inn & Suites, an Ascend Collection Hotel