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

St. Leonard Holiday Rentals

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Our top choices for St. Leonard holiday rentals

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, (3 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is AU$409
includes taxes & fees
6 Aug - 7 Aug
3-bedroom house in soothing Saint Leonard with AC for relaxing stays

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 AU$1,134
includes taxes & fees
6 Aug - 7 Aug
Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

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 AU$1,624
includes taxes & fees
5 Aug - 6 Aug
Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub

Lakefront Cabin Near Solomons Island w/ Hot Tub
3.0 star property
Lusby
The price is AU$1,637
includes taxes & fees
27 July - 28 July
Lakefront Cabin Near Solomons Island w/ Hot Tub

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, (12 reviews)
"The owner was very nice "
United States
karen
The price is AU$380
includes taxes & fees
6 Aug - 7 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (55 reviews)
"Cute, sweet spot with a peaceful vibe and lovely view!"
United States
Melinda S.
The price is AU$452
includes taxes & fees
6 Aug - 7 Aug
Soul Oasis - home on the Chesapeake Bay

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 AU$518
includes taxes & fees
6 Aug - 7 Aug
Bright and airy waterfront getaway

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$645
includes taxes & fees
25 July - 26 July
Plum Point Cottage #17

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
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 AU$964
includes taxes & fees
13 Aug - 14 Aug
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 AU$1,427
includes taxes & fees
12 Aug - 13 Aug
Waterfront home on Mill Creek-5BR-3bath-Hot tub, Kayaks & private dock

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 AU$1,190
includes taxes & fees
5 Aug - 6 Aug
4-BR Waterfront Turret Home

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 AU$1,044
includes taxes & fees
26 July - 27 July
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

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 AU$820
includes taxes & fees
28 July - 29 July
Anne & Fred`s Leonardtown Home W/ Arcade room!

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 AU$835
includes taxes & fees
29 July - 30 July
Sunset Breezes - quiet waterfront retreat

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 AU$720
includes taxes & fees
13 Aug - 14 Aug
Beachside Oasis with Beach Passes & King Suite by A Haven Away

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 AU$1,199
includes taxes & fees
18 Aug - 19 Aug
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Coles Point Marina

Coles Point Marina
2.0 star property
Hague
The price is AU$466
includes taxes & fees
29 July - 30 July
Coles Point Marina

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AU$1,029
includes taxes & fees
26 July - 27 July
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

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)
"We had a wonderful stay! Beautiful waterfront home with a brand new pier overlooking the river and a perfect sunset. Quiet location, perfectly appointed and great location next to parks, St Mary’s City and campus. Highly recommend!"
United States
Kurt O.
The price is AU$537
includes taxes & fees
27 July - 28 July
Waterfront Retreat | New Private Pier | Remodeled | Epic Sunset Views

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is AU$1,311
includes taxes & fees
29 July - 30 July
'the Bayside Escape' Remote Chesapeake Bay Estate
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

Everything you need to know about St. Leonard holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the St. Leonard holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect St. Leonard holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

St. Leonard holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in St. Leonard. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A St. Leonard holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of St. Leonard holiday rentals we have selected for you start as low as AU$380 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on St. Leonard rentals

At Expedia, we put the best St. Leonard holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top St. Leonard rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream St. Leonard holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around St. Leonard. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Private Chesapeake Bay Beach community…love to feel the sand between your toes?: 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 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, 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 19 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 Jefferson Patterson Park and Museum and Northern Chesapeake Bay.

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.