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

St. Leonard Vacation Rentals

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Our top choices for St. Leonard vacation rentals

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, (6 reviews)
"Lovely!! Perfect for our family for a weekend adventure. Very fun spaces with everything you need. The morning stroll to see the sunrise over the water was divine! Thank you!"
United States
Kate J.
The price is CA $184
CA $378 total
includes taxes & fees
Aug 31 - Sep 1
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

2. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.4 out of 10, Exceptional, (14 reviews)
"The owner was very nice "
United States
karen
The price is CA $235
CA $398 total
includes taxes & fees
Aug 25 - Aug 26
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (57 reviews)
"Cute A-frame with all the necessities!"
United States
Anonymous traveller
The price is CA $217
CA $445 total
includes taxes & fees
Sep 8 - Sep 9
Soul Oasis - home on the Chesapeake Bay

4. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (22 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is CA $318
CA $533 total
includes taxes & fees
Aug 25 - Aug 26
Bright and airy waterfront getaway

5. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $376
CA $635 total
includes taxes & fees
Aug 31 - Sep 1
Plum Point Cottage #17

6. 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, (22 reviews)
"Lovely ! "
United States
Ellen B.
The price is CA $136
CA $479 total
includes taxes & fees
Aug 26 - Aug 27
Beachside Oasis with Beach Passes & King Suite by A Haven Away

7. 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 CA $284
CA $732 total
includes taxes & fees
Sep 9 - Sep 10
Family Beach House: Spacious Deck, Grill & Views

8. 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 CA $598
CA $1,608 total
includes taxes & fees
Aug 27 - Aug 28
Lakefront Cabin Near Solomons Island w/ Hot Tub

9. 4-BR Waterfront Turret Home

4-BR Waterfront Turret Home
Solomons
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house. Beautiful scenery. Everything was perfect. "
United States
Thomas S.
The price is CA $414
CA $994 total
includes taxes & fees
Sep 8 - Sep 9
4-BR Waterfront Turret Home

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, Exceptional, (13 reviews)
"The home was lovely and very quiet location. My sister and I were caring for our mom after discharge from hospital and it was very convenient. Would stay there again. "
United States
Tova A.
The price is CA $638
CA $1,192 total
includes taxes & fees
Aug 27 - Aug 28
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

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, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is CA $216
CA $667 total
includes taxes & fees
Sep 14 - Sep 15
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

12. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is CA $706
CA $1,580 total
includes taxes & fees
Aug 24 - Aug 25
Lakefront Cabin Near Solomons Island w/ Hot Tub

13. Anne & Fred`s Leonardtown Home W/ Arcade room!

Anne & Fred`s Leonardtown Home W/ Arcade room!
Leonardtown
9.2 out of 10, Wonderful, (7 reviews)
"Amazing place to stay. Very Very clean ! Great location. Definitely will book this place again "
United States
Christy C.
The price is CA $330
CA $809 total
includes taxes & fees
Aug 26 - Aug 27
Anne & Fred`s Leonardtown Home W/ Arcade room!

14. 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, (2 reviews)
"We loved our stay! Lovely home, beautiful view"
United States
Sarah R.
The price is CA $642
CA $1,379 total
includes taxes & fees
Sep 17 - Sep 18
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

15. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is CA $267
CA $418 total
includes taxes & fees
Aug 25 - Aug 26
Coles Point Marina

16. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is CA $318
CA $382 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront Getaway with Dock

17. 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, (13 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is CA $242
CA $530 total
includes taxes & fees
Sep 9 - Sep 10
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

18. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (53 reviews)
"My husband and I had a great 3 day getaway here. The view was spectacular! The convenience from walking to the dock to the house was awesome! The only “bad” thing I would say is the water….it has an awful sulfur smell that is very strong. Overall, we loved our stay & would stay here again!"
United States
Ashley D.
The price is CA $242
CA $470 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Virginia Potomac Riverfront Cottage

19. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is CA $536
CA $671 total
includes taxes & fees
Sep 8 - Sep 9
Sunset Breezes - quiet waterfront retreat

20. 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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $451
CA $846 total
includes taxes & fees
Sep 2 - Sep 3
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
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

Find out more about St. Leonard

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with St. Leonard. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in St. Leonard?

Yes, we offer vacation rentals close to the most popular points of interest in St. Leonard, or you can choose a more secluded option if you want a relaxing place to stay. St. Leonard is known for its shopping and sporting events. Make sure you have time to check out the restaurants and wineries during your trip.

What's the top vacation rental that St. Leonard has to offer?

3-bedroom house in soothing Saint Leonard with AC for relaxing stays: Visitors give good reviews to this St. Leonard vacation home rental, which offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in St. Leonard?

With 20 Expedia vacation rentals, you're sure to find just the right place for your St. Leonard stay.

What’s there to see and do in St. Leonard?

Matoaka Beach and Flag Ponds Nature Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Jefferson Patterson Park and Museum and Northern Chesapeake Bay.

What’s a vacation rental in St. Leonard like?

Vacation rentals are privately owned properties you can book for a couple of days or more in St. Leonard. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip or a small group gathering.