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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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, (5 reviews)
The price is ￥21,499
￥44,396 total
includes taxes & fees
Aug 18 - Aug 19
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Exterior

2. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (56 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is ￥24,843
￥51,148 total
includes taxes & fees
Sep 8 - Sep 9
Soul Oasis - home on the Chesapeake Bay
Beach nearby

3. 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 ￥15,651
￥55,589 total
includes taxes & fees
Aug 13 - Aug 14
Beachside Oasis with Beach Passes & King Suite by A Haven Away
Outdoor dining

4. 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 ￥24,939
￥77,270 total
includes taxes & fees
Sep 8 - Sep 9
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Coffee/tea maker, fridge, microwave, oven

5. 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 ￥36,628
￥42,877 total
includes taxes & fees
Aug 17 - Aug 18
Waterfront Getaway with Dock
Property grounds

6. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (21 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 ￥36,628
￥61,783 total
includes taxes & fees
Aug 17 - Aug 18
Bright and airy waterfront getaway
Property grounds

7. 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 ￥27,073
￥46,228 total
includes taxes & fees
Aug 18 - Aug 19
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Outdoor dining

8. 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 ￥61,311
￥77,340 total
includes taxes & fees
Sep 8 - Sep 9
Sunset Breezes - quiet waterfront retreat
Interior

9. Cozy Virginia Potomac Riverfront Cottage

Cozy Virginia Potomac Riverfront Cottage
Hague
9.6 out of 10, Exceptional, (51 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 ￥27,869
￥54,580 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Virginia Potomac Riverfront Cottage
Cottage, 2 Bedrooms, Kitchen | Exterior

10. Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥30,748
￥48,180 total
includes taxes & fees
Aug 13 - Aug 14
Coles Point Marina
Interior

11. 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, (11 reviews)
"Beautiful sunset and very comfortable rooms. "
United States
Andrea B.
The price is ￥33,761
￥68,188 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Coffee/tea maker, fridge, microwave, oven

12. 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 ￥37,408
￥92,953 total
includes taxes & fees
Aug 16 - Aug 17
Anne & Fred`s Leonardtown Home W/ Arcade room!
Property grounds

13. 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 ￥73,574
￥137,408 total
includes taxes & fees
Aug 16 - Aug 17
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay
House (3 Bedrooms) | Interior

14. Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is ￥81,377
￥182,230 total
includes taxes & fees
Aug 24 - Aug 25
Lakefront Cabin Near Solomons Island w/ Hot Tub
Interior

15. Rustic 3BR Waterfront Cabin with Firepit + Dock Access

Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Hague
10.0 out of 10, Exceptional, (1 review)
"We were going to an evening event at Stratford Hall (about 25 min away). There is so much history in the area. Beautiful spot on the river. The screened in porch was the bomb! Huge. So relaxing. Well stocked. Easy check out. Do pay attention to room configuration. The bedroom with twins was a loft like area but had the nicer bathroom. We used the kayaks. Had everything we needed. Host communication was great despite Vrbo platform was a challenge."
United States
Paige
The price is ￥50,164
￥90,101 total
includes taxes & fees
Sep 9 - Sep 10
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Smart TV

16. 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 ￥61,013
￥108,395 total
includes taxes & fees
Aug 19 - Aug 20
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV, books

17. 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 ￥47,775
￥115,483 total
includes taxes & fees
Sep 9 - Sep 10
4-BR Waterfront Turret Home
Exterior

18. Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (5 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 ￥54,623
￥127,087 total
includes taxes & fees
Aug 17 - Aug 18
Charming Waterfront 3-bedroom house in Piney Point
Pool

19. 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 ￥29,621
￥81,396 total
includes taxes & fees
Sep 2 - Sep 3
Family Beach House: Spacious Deck, Grill & Views
Exterior

20. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is ￥43,396
￥73,910 total
includes taxes & fees
Aug 13 - Aug 14
Plum Point Cottage #17
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

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

10/10 Excellent
"At first Glance, the place was so clean and well lite in and outside. The staff were extremely kind and helpful. Breakfast was included and nice."
Fran 1-night trip
Posted 1 hour ago
avid hotel California - Lexington Park by IHG

Find out more about St. Leonard

Search for holiday rentals in St. Leonard on Expedia! You can easily find your home rentals, villas, holiday apartments in St. Leonard using one of the methods below:

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Look no further and take a look at our great range of rental properties in St. Leonard!

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 Northern Chesapeake Bay are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Patuxent River and 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.