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
  • Be picky

    Search almost a million properties worldwide

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for St. Leonard vacation homes

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 572
AED 1,062 total
includes taxes & fees
18 Nov - 19 Nov
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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 1,343 total
includes taxes & fees
12 Nov - 13 Nov
Bright and airy waterfront getaway

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)
"Very clean and nice property"
United States
Ben W.
Family Beach House: Spacious Deck, Grill & Views

4. 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 2,986 total
includes taxes & fees
8 Nov - 9 Nov
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

5. 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 1,590
AED 3,965 total
includes taxes & fees
15 Nov - 16 Nov
Lakefront Cabin Near Solomons Island w/ Hot Tub

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, (4 reviews)
"Dude. This is what I always hope a rental property will be. Comfy beds, best stocked kitchen, working hot tub, beautiful waterfront area with kayaks and a dock. And our mini golden doodle could come too?! It was absolute perfection."
United States
Dani B.
The price is AED 1,293
AED 3,398 total
includes taxes & fees
10 Nov - 11 Nov
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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 2,581 total
includes taxes & fees
9 Nov - 10 Nov
4-BR Waterfront Turret Home

8. 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 533
AED 1,145 total
includes taxes & fees
15 Nov - 16 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AED 323
AED 1,091 total
includes taxes & fees
12 Nov - 13 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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 AED 593
AED 1,678 total
includes taxes & fees
16 Nov - 17 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

11. 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 1,061
AED 1,837 total
includes taxes & fees
8 Nov - 9 Nov
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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, (20 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is AED 661
AED 1,311 total
includes taxes & fees
9 Nov - 10 Nov
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

13. 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 1,432
AED 2,925 total
includes taxes & fees
1 Dec - 2 Dec
2 Acre Oasis with Private Beach! Family and dog friendly!

14. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (9 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 1,018
AED 2,427 total
includes taxes & fees
9 Nov - 10 Nov
Charming Waterfront 3-bedroom house in Piney Point

15. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (69 reviews)
"Excellent stay! Just as described! Very quiet, private location."
United States
Mills Family A.
The price is AED 810
AED 929 total
includes taxes & fees
8 Nov - 9 Nov
Waterfront Getaway with Dock

16. 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 1,792
AED 3,035 total
includes taxes & fees
7 Dec - 8 Dec
Tranquil Modern Farmhouse

17. Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks

Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
Montross
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is AED 701
AED 1,713 total
includes taxes & fees
18 Nov - 19 Nov
Waterfront Home w/Private Hot Tub · Game Room · Fire Pit · Kayaks
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.

Learn more about St. Leonard

Explore the Calvert Marine Museum's river otters and fossil exhibits, then enjoy fresh seafood at waterfront restaurants along Patuxent River. Nearby Flag Ponds Nature Park offers peaceful beaches where you can hunt for prehistoric shark teeth during low tide.

A forest with pink and white flowers and sunlight filtering through the trees.

Top reviews in St. Leonard