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

St. Leonard Vacation Rentals

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for St. Leonard vacation rentals

TV, fireplace

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)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AED 476
AED 987 total
includes taxes & fees
22 Sep - 23 Sep
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Property grounds

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
9.2 out of 10, Wonderful, (15 reviews)
"The owner was very nice "
United States
karen
The price is AED 624
AED 1,066 total
includes taxes & fees
25 Aug - 26 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

3. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is AED 577
AED 1,187 total
includes taxes & fees
15 Sep - 16 Sep
Soul Oasis - home on the Chesapeake Bay
Property grounds

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 AED 760
AED 1,320 total
includes taxes & fees
25 Aug - 26 Aug
Bright and airy waterfront getaway
Exterior

5. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,705 total
includes taxes & fees
25 Aug - 26 Aug
Plum Point Cottage #17
Beach nearby

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 AED 258
AED 1,144 total
includes taxes & fees
27 Aug - 28 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Pool

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 AED 713
AED 1,902 total
includes taxes & fees
9 Sep - 10 Sep
Family Beach House: Spacious Deck, Grill & Views
Interior

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 AED 1,590
AED 4,269 total
includes taxes & fees
25 Aug - 26 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
Smart TV, books

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 AED 1,102
AED 2,593 total
includes taxes & fees
8 Sep - 9 Sep
4-BR Waterfront Turret Home
Property grounds

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, (14 reviews)
"Nice house in a great location. Great for groups."
United States
Anonymous traveler
The price is AED 1,697
AED 3,169 total
includes taxes & fees
25 Aug - 26 Aug
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
Outdoor dining

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 AED 666
AED 1,891 total
includes taxes & fees
20 Sep - 21 Sep
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
House (3 Bedrooms) | Interior

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 AED 1,877
AED 4,203 total
includes taxes & fees
25 Aug - 26 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub
Coffee/tea maker, fridge, microwave, oven

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 AED 878
AED 2,164 total
includes taxes & fees
25 Aug - 26 Aug
Anne & Fred`s Leonardtown Home W/ Arcade room!
TV, fireplace, video games, books

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 AED 1,697
AED 3,637 total
includes taxes & fees
17 Sep - 18 Sep
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock
Cottage, 2 Bedrooms, Kitchen | Exterior

15. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AED 709
AED 1,111 total
includes taxes & fees
25 Aug - 26 Aug
Coles Point Marina
Coffee/tea maker, fridge, microwave, oven

16. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (65 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AED 845
AED 1,024 total
includes taxes & fees
26 Aug - 27 Aug
Waterfront Getaway with Dock
Interior

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 AED 643
AED 1,417 total
includes taxes & fees
9 Sep - 10 Sep
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Interior

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 AED 643
AED 1,259 total
includes taxes & fees
25 Aug - 26 Aug
Cozy Virginia Potomac Riverfront Cottage
Outdoor dining

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 AED 1,609
AED 2,015 total
includes taxes & fees
8 Sep - 9 Sep
Sunset Breezes - quiet waterfront retreat
Smart TV

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 AED 1,244
AED 2,303 total
includes taxes & fees
2 Sep - 3 Sep
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

The Inn at Leonardtown, an Ascend Collection Hotel

The Inn at Leonardtown, an Ascend Collection Hotel

10/10 Excellent
"A nice clean large room."
Raymond 2-night trip
Posted 1 hour ago
The Inn at Leonardtown, an Ascend Collection Hotel

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.