Book Holiday Homes in St. Leonard

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in St. Leonard

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Bay view from Calvert Cliffs, Solomons Island & State Park nearby

Lusby
Located in Lusby, this vacation home is on a lake, within a 10-minute drive of Cove Point Park and Calvert Cliffs State Park.
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

Chesapeake Beach
Located in Chesapeake Beach, this vacation home is on the waterfront, a 1-minute drive from Bruce Gabrielson's Surf Art Gallery and Museum and 6 minutes from ...
Rising Sun Bay View Cottage
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
Save an average of 15% on thousands of hotels when you're signed in
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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 Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
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
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 calvART Gallery.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Located in Lusby, this vacation home is on the waterfront, a 4-minute drive from Drum Point Lake and 6 minutes from Seahorse Beach.
Waterfront Wildlife Retreat on the Patuxent River
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Cambridge
The price is AU$799 per night from 1 Sept to 2 Sept
AU$799
1 Sept - 2 Sept
includes taxes & fees
Located in Cambridge, this vacation home is on the waterfront, within a 15-minute drive of Spocott Windmill and Ragged Island.
Beautiful Waterfront Retreat in Cambridge!
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
Don't see what you're looking for?
See all available properties in St. Leonard
View all properties
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
240 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$799
Popular accommodation
Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Rising Sun Bay View Cottage, Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, The Blue Crab Beach House - Free beach passes , Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Waterfront Wildlife Retreat on the Patuxent River , Beautiful Waterfront Retreat in Cambridge!, WATERFRONT!!! The River's Roost on The Patuxent River

Top trending hotels in St. Leonard

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!
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is AU$244 per night from 1 Sept to 2 Sept
AU$244
1 Sept - 2 Sept
includes taxes & fees
With a stay at Solomons Inn Resort & Marina in Solomons, you'll be a 3-minute walk from Southern Branch Library and 11 minutes by foot from Drum Point ...
Solomons Inn Resort & Marina
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$247 per night from 20 Aug to 21 Aug
AU$247
20 Aug - 21 Aug
includes taxes & fees
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
Save an average of 15% on thousands of hotels when you're signed in
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 11 Sept to 12 Sept
AU$158
11 Sept - 12 Sept
includes taxes & fees
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
Don't see what you're looking for?
See all available properties in St. Leonard
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.