Book Holiday Homes in St. Leonard

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Featured Holiday Homes in St. Leonard

The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

North Beach
Stay at this vacation home in Owings. Enjoy a garden, patios, and air conditioning. Popular attractions Bayside History Museum and Chesapeake Beach Water Park ...
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp

Drayden
Stay at this vacation home in Drayden. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Dennis Point Marina and Saint George Island Beach ...
Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp
Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

Chesapeake Beach
Book a stay at this beach vacation home in Chesapeake Beach. Enjoy a beach locale, a garden, and laundry facilities. Popular attractions Bruce Gabrielson's Surf ...
Rising Sun Bay View Cottage
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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
Stay at this vacation home in Cambridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
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
Stay at this vacation home in North Beach. Enjoy free WiFi, a water park, and a garden. Popular attractions Bayside History Museum and Chesapeake Beach Water ...
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
Book a stay at this beach vacation home in Port Republic. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Matoaka Beach and Long Beach are ...
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby
Stay at this vacation home in Lusby. Enjoy free WiFi, a water park, and laundry facilities. Popular attractions Seahorse Beach and Drum Point Lake are located ...
Bay view from Calvert Cliffs, Solomons Island & State Park nearby
Waterfront Wildlife Retreat on the Patuxent River

Waterfront Wildlife Retreat on the Patuxent River

Lusby
Stay at this vacation home in Lusby. Enjoy free WiFi, laundry facilities, and patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
Waterfront Wildlife Retreat on the Patuxent River
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River

Cobb Island
Stay at this vacation home in Cobb Island. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Colonial Beach and Saint Clements Island-Potomac ...
Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac River
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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
236 Holiday Homes
Lowest Price
NZ$174
Highest Price
NZ$285
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, Spacious Waterfront Home secluded on 60 ac with Beach and Boat Ramp, Rising Sun Bay View Cottage, 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, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Waterfront Wildlife Retreat on the Patuxent River , Waterfront Cottage with Pier & Boatlift on the Beautiful Potomac 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
Stay at this vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Perigeaux Vineyards and Winery and Jefferson ...
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 NZ$268 per night from 1 Sept to 2 Sept
NZ$268
1 Sept - 2 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Solomons. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Southern Branch Library and Drum ...
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 NZ$285 per night from 5 Aug to 6 Aug
NZ$285
5 Aug - 6 Aug
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
Rod 'N' Reel Resort
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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 NZ$174 per night from 1 Sept to 2 Sept
NZ$174
1 Sept - 2 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in California. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
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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.