St Leonards beach at low tide

St. Leonard Holiday Rentals

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Check prices for these dates

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

Our top choices for St. Leonard holiday 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 HK$1,207
HK$2,483 total
includes taxes & fees
17 Jun - 18 Jun
Soul Oasis - home on the Chesapeake Bay
Exterior

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is HK$1,681
HK$2,554 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,199
HK$2,060 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,452
HK$3,517 total
includes taxes & fees
30 Jun - 1 Jul
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 HK$3,017
HK$5,081 total
includes taxes & fees
6 Jul - 7 Jul
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 HK$1,802
HK$2,184 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$2,362
HK$2,828 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$2,703
HK$3,342 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,622
HK$2,724 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,119
HK$3,624 total
includes taxes & fees
17 Jun - 18 Jun
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 HK$2,022
HK$3,740 total
includes taxes & fees
22 Jun - 23 Jun
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 HK$2,356
HK$3,034 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$2,688
HK$4,983 total
includes taxes & fees
21 Jun - 22 Jun
Charming Waterfront 3-bedroom house in Piney Point
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 HK$2,186
HK$4,814 total
includes taxes & fees
15 Jul - 16 Jul
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 HK$1,345
HK$3,714 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$3,244
HK$8,209 total
includes taxes & fees
10 Jul - 11 Jul
Lakefront Cabin near Solomons Island w/ Hot Tub
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 HK$3,463
HK$7,276 total
includes taxes & fees
5 Jul - 6 Jul
'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 HK$2,431
HK$4,404 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$3,173
HK$5,910 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$2,233
HK$4,344 total
includes taxes & fees
15 Jun - 16 Jun
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 1 day 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 holiday rental in St. Leonard?

Yes, there are holiday rentals close to the most popular sights in St. Leonard, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that St. Leonard has to offer?

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW: This holiday home rental outside of St. Leonard is located on the waterfront, and has a patio, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in St. Leonard?

With 18 Expedia holiday rentals, you're guaranteed 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 holiday rental in St. Leonard like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in St. Leonard. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family trips.