St Leonards beach at low tide

St. Leonard Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for St. Leonard vacation rentals

Exterior

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (50 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is ￥25,762
￥52,071 total
includes taxes & fees
Jun 17 - Jun 18
Soul Oasis - home on the Chesapeake Bay
Cottage, 2 Bedrooms, Kitchen | Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is ￥31,582
￥49,158 total
includes taxes & fees
Jun 15 - Jun 16
Coles Point Marina
Property grounds

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, (9 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is ￥24,517
￥42,472 total
includes taxes & fees
Jun 14 - Jun 15
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (21 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is ￥25,151
￥67,732 total
includes taxes & fees
Jun 24 - Jun 25
Walk to Beach! King Bed & Free Beach Passes
Terrace/patio

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 ￥61,604
￥103,760 total
includes taxes & fees
Jul 6 - Jul 7
Rustic 3BR Waterfront Cabin with Firepit + Dock Access
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (57 reviews)
"Great place, will stay again"
United States
Matt S.
The price is ￥36,802
￥44,607 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront Getaway with Dock
Sun loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is ￥48,243
￥57,752 total
includes taxes & fees
Jun 14 - Jun 15
Cottage Located on the Patuxent River!
Exterior

2 Bedroom Cottage at Coles Point Marina

2 Bedroom Cottage at Coles Point Marina
Hague
The price is ￥55,203
￥67,722 total
includes taxes & fees
Jun 14 - Jun 15
2 Bedroom Cottage at Coles Point Marina
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 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 ￥36,802
￥60,551 total
includes taxes & fees
Jun 15 - Jun 16
Bright and airy waterfront getaway
Outdoor dining

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, (36 reviews)
"Everything was as expected, lovely spot even with lots of snow and ice!"
United States
Becky S.
The price is ￥29,867
￥82,708 total
includes taxes & fees
Jun 15 - Jun 16
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior

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, (9 reviews)
"Everything was very clean and well put together. Loved the view!"
United States
Minji S.
The price is ￥64,484
￥102,806 total
includes taxes & fees
Jun 21 - Jun 22
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views
Fridge, microwave, oven, stovetop

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is ￥48,115
￥62,513 total
includes taxes & fees
Jun 14 - Jun 15
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Exterior

Charming Waterfront 3-bedroom house in Piney Point

Charming Waterfront 3-bedroom house in Piney Point
Piney Point
10.0 out of 10, Exceptional, (4 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 ￥54,883
￥101,760 total
includes taxes & fees
Jun 21 - Jun 22
Charming Waterfront 3-bedroom house in Piney Point
Pool

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ￥45,668
￥99,680 total
includes taxes & fees
Jul 13 - Jul 14
Family Beach House: Spacious Deck, Grill & Views
Sun loungers, beach towels

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK

Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Montross
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful home, very clean and comfy "
United States
Julie P.
The price is ￥27,497
￥75,944 total
includes taxes & fees
Jun 15 - Jun 16
Waterfront, Kayak, Beach, Game room, Potomac 2hr DC, Dogs+EV OK
Interior

Lakefront Cabin near Solomons Island w/ Hot Tub

Lakefront Cabin near Solomons Island w/ Hot Tub
Lusby
10.0 out of 10, Exceptional, (1 review)
"We had such a wonderful stay at Diana’s lake house! The view of the lake is absolutely beautiful waking up to that peaceful scenery every morning was one of the highlights of our trip.The property has a charming rustic feel while still offering all the amenities you could need. It felt cozy and comfortable, yet fully equipped for a relaxing getaway. We especially loved being able to kayak right from the area such a perfect way to enjoy the water and the surroundings.Diana was an exceptional...
United States
rakesh s.
The price is ￥68,004
￥171,463 total
includes taxes & fees
Jun 15 - Jun 16
Lakefront Cabin near Solomons Island w/ Hot Tub
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is ￥70,724
￥148,574 total
includes taxes & fees
Jul 5 - Jul 6
'the Bayside Escape' Remote Chesapeake Bay Estate
Property grounds

Secluded Woodland Waterfront Retreat

Secluded Woodland Waterfront Retreat
Solomons
10.0 out of 10, Exceptional, (12 reviews)
"The host was very communicative, the house was very clean and comfortable, and the river views were beautiful!"
United States
Meghan H.
The price is ￥49,643
￥89,937 total
includes taxes & fees
Jun 15 - Jun 16
Secluded Woodland Waterfront Retreat
Smart TV, fireplace, computer monitors, printers

Tranquil Modern Farmhouse

Tranquil Modern Farmhouse
Waldorf
9.2 out of 10, Wonderful, (10 reviews)
"The host communicated immediately if needed. The house has practically everything a family needs. Fully stocked kitchen for meal prep, wonderful towels and memory foam beds. A wonderful rental."
United States
Kymme
The price is ￥64,804
￥120,515 total
includes taxes & fees
Jun 14 - Jun 15
Tranquil Modern Farmhouse
Smart TV, books

Peaceful Waterfront Retreat for Bird Lovers- Close to DC

Peaceful Waterfront Retreat for Bird Lovers- Close to DC
Leonardtown
9.8 out of 10, Exceptional, (6 reviews)
"Beautiful property in a peaceful neighborhood. Great location! "
United States
R. L.
The price is ￥48,803
￥92,596 total
includes taxes & fees
Jun 16 - Jun 17
Peaceful Waterfront Retreat for Bird Lovers- Close to DC
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

SureStay by Best Western Prince Frederick

SureStay by Best Western Prince Frederick

10/10 Excellent
"Very clean and neat, great price and location. Very close to lots of good eats and beautiful area to explore."
Shawn 1-night trip
Posted 3 hours ago
SureStay by Best Western Prince Frederick

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?

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW: This vacation home rental near St. Leonard is located on the waterfront and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in St. Leonard?

With 18 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 Northern Chesapeake Bay and Patuxent River.

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.