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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 ¥17,258
¥37,276 total
includes taxes & fees
Nov 16 - Nov 17
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is ¥30,904
¥62,996 total
includes taxes & fees
Nov 20 - Nov 21
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

3. 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 ¥36,450
¥57,956 total
includes taxes & fees
Nov 11 - Nov 12
Bright and airy waterfront getaway

4. 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.
The price is ¥22,437
¥60,413 total
includes taxes & fees
Dec 2 - Dec 3
Family Beach House: Spacious Deck, Grill & Views

5. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Lusby
9.8 out of 10, Exceptional, (16 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
The price is ¥73,001
¥128,466 total
includes taxes & fees
Nov 14 - Nov 15
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

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 ¥68,418
¥169,906 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront Cabin Near Solomons Island w/ Hot Tub

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, (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 ¥55,620
¥145,009 total
includes taxes & fees
Nov 24 - Nov 25
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ¥12,492
¥47,028 total
includes taxes & fees
Nov 12 - Nov 13
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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.
The price is ¥47,403
¥111,018 total
includes taxes & fees
Nov 22 - Nov 23
4-BR Waterfront Turret Home

10. 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 ¥22,911
¥48,907 total
includes taxes & fees
Nov 11 - Nov 12
The Cozy Crab- Your Charming Haven in Lovely North Beach!

11. 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 ¥25,511
¥72,200 total
includes taxes & fees
Nov 16 - Nov 17
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

12. 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 ¥45,249
¥78,614 total
includes taxes & fees
Dec 2 - Dec 3
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 ¥61,807
¥132,941 total
includes taxes & fees
Dec 1 - Dec 2
2 Acre Oasis with Private Beach! Family and dog friendly!

14. 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, (21 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is ¥28,442
¥56,403 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

15. 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 ¥41,367
¥101,534 total
includes taxes & fees
Nov 15 - Nov 16
Charming Waterfront 3-bedroom house in Piney Point

16. 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 ¥34,841
¥40,114 total
includes taxes & fees
Nov 17 - Nov 18
Waterfront Getaway with Dock

17. 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 ¥65,985
¥116,864 total
includes taxes & fees
Nov 16 - Nov 17
Tranquil Modern Farmhouse

18. 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 ¥30,265
¥74,760 total
includes taxes & fees
Nov 15 - Nov 16
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