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!
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
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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!
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!
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!
Sea Glass Beach House!  Large sand beach, dock and hot tub! Pets welcome!

Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!

Hague
Located in Hague, this vacation home is by the ocean, within a 15-minute drive of Coles Point Marina and Hague Winery.
Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome!
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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman State Park ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
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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
171 Holiday Homes
Lowest Price
AU$226
Highest Price
AU$226
Popular accommodation
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Screened Patio, Deck & Grill: Saint Inigoes Home!, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!, Safe Harbor at Herring Bay - Your Chesapeake Bay adventure awaits! , Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Sea Glass Beach House! Large sand beach, dock and hot tub! Pets welcome! , The Blue Crab Beach House - Free beach passes , The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Top trending hotels in St. Leonard

5 bedroom, 8 bed, 3 story house a block from beach

5 bedroom, 8 bed, 3 story house a block from beach

Saint Leonard
Located in St. Leonard, this vacation home is in a rural location, within a 15-minute walk of Flag Harbor Marina and Flag Ponds Nature Park.
5 bedroom, 8 bed, 3 story house a block from beach
WATERFRONT!!! The River's Roost on The Patuxent River

WATERFRONT!!! The River's Roost on The Patuxent River

Saint Leonard
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Gray's Road Dog Park and Battle Creek Cypress Swamp Sanctuary.
WATERFRONT!!! The River's Roost on The Patuxent River
New! Cozy River Cottage with great views of the water!

New! Cozy River Cottage with great views of the water!

Saint Leonard
Located in St. Leonard, this vacation home is on the waterfront, within a 15-minute drive of Perigeaux Vineyards and Winery and Jefferson Patterson Park and ...
New! Cozy River Cottage with great views of the water!
Save an average of 15% on thousands of hotels when you're signed in
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave, Chesapeake Beach, MD
Fully refundableReserve now, pay when you stay
The price is AU$226 per night from 14 Mar to 15 Mar
AU$226
includes taxes & fees
14 Mar - 15 Mar
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
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See all available properties in St. Leonard
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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.