Book Holiday Homes in St. Leonard

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Featured Holiday Homes in St. Leonard

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Tracys Landing
This vacation home is 3.1 mi (5 km) from Upper Yough River and 4.8 mi (7.7 km) from Bayside History Museum.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Screened Patio, Deck & Grill: Saint Inigoes Home!

Screened Patio, Deck & Grill: Saint Inigoes Home!

St Inigoes
Located in Saint Inigoes, this vacation home is on the waterfront, a 3-minute drive from Saint Inigoes State Forest and 7 minutes from Cardinal Gibbons ...
Screened Patio, Deck & Grill: Saint Inigoes Home!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard
With a stay at this vacation home in St. Leonard, you'll be near the beach, just steps from Jefferson Patterson Park and Museum and a 3-minute drive from Perigeaux ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
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Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!

North Beach
Located in North Beach, this vacation home is within a 10-minute drive of Bayside History Museum and Upper Yough River.
Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits!
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
Located in North Beach, this vacation home is by the sea, within a 5-minute drive of Bayside History Museum and Chesapeake Beach Water Park.
The Blue Crab Beach House - Free beach passes
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cambridge
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 12 minutes by car from Spocott Windmill.
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Stunning  Chesapeake view from almost ever room, private  15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
Located in Port Republic, this vacation home is on the waterfront, within a 10-minute drive of R&J's PlayPark and Battle Creek Cypress Swamp Sanctuary.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Belle of the Chesapeake Bay

Belle of the Chesapeake Bay

Lusby
When you stay at this vacation home in Lusby, you'll be within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Belle of the Chesapeake Bay
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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.

St. Leonard Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our St. Leonard vacation homes are the perfect way for you to wing it.

Holiday houses in St. Leonard let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of St. Leonard in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local St. Leonard adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in St. Leonard with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of St. Leonard vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

St. Leonard Holiday Homes essential information

Accommodation
170 Holiday Homes
Lowest Price
AU$164
Highest Price
AU$206
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Screened Patio, Deck & Grill: Saint Inigoes Home!, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits! , The Blue Crab Beach House - Free beach passes , Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Belle of the Chesapeake Bay

Top trending hotels in St. Leonard

Rod 'N' Reel Resort

Rod 'N' Reel Resort

3 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 2 Feb to 3 Feb
AU$196
includes taxes & fees
2 Feb - 3 Feb
When you stay at Rod 'N' Reel Resort in Chesapeake Beach, you'll be on the waterfront, just steps from Chesapeake Beach Railway Museum and 3 minutes by foot ...
Rod 'N' Reel Resort
Springhill Suites by Marriott Prince Frederick

Springhill Suites by Marriott Prince Frederick

3 out of 5
75 Sherry Lane, Prince Frederick, MD
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 26 Jan to 27 Jan
AU$206
includes taxes & fees
26 Jan - 27 Jan
With a stay at Springhill Suites by Marriott Prince Frederick in Prince Frederick, you'll be a 1-minute walk from R&J's PlayPark and 7 minutes by foot from calvART ...
Springhill Suites by Marriott Prince Frederick
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is AU$164 per night from 31 Jan to 1 Feb
AU$164
includes taxes & fees
31 Jan - 1 Feb
Located in California, La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent is within a 5-minute drive of San Souci Shopping Center and Dunleigh Neighborhood ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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Holiday Inn Express Prince Frederick, an IHG Hotel

Holiday Inn Express Prince Frederick, an IHG Hotel

2.5 out of 5
355 Merrimac Ct, Prince Frederick, MD
Fully refundable
The price is AU$186 per night from 26 Jan to 27 Jan
AU$186
includes taxes & fees
26 Jan - 27 Jan
Located in Prince Frederick, Holiday Inn Express Prince Frederick, an IHG Hotel is within a 10-minute drive of Running Hare Vineyard and Battle Creek Cypress ...
Holiday Inn Express Prince Frederick, an IHG Hotel
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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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^Subject to availability and chosen travel dates.