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 MD
Stay at this holiday home in Owings. Enjoy a garden, patios and air conditioning. Popular attractions Bayside History Museum and Chesapeake Beach Water Park ...
Opens in a new windowThe Cozy Crab- Your Charming Haven in Lovely North Beach!
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach MD
Stay at this holiday home in North Beach. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bayside History Museum and Chesapeake Beach ...
Opens in a new windowThe Blue Crab Beach House - Free beach passes
"La Licorne" Waterfront Beach Cottage

"La Licorne" Waterfront Beach Cottage

North Beach MD
Stay at this holiday home in North Beach. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Bayside History Museum and Chesapeake ...
Opens in a new window"La Licorne" Waterfront Beach Cottage
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4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick

Prince Frederick MD
Stay at this holiday home in Prince Frederick. Enjoy laundry facilities, in-room jetted baths and an in-room coffee maker. Popular attractions R&J's PlayPark ...
Opens in a new window4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick
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 MD
Stay at this holiday home in Cambridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
Stay at this holiday home in Tilghman. Enjoy a garden, laundry facilities and balconies. Popular attractions Tilghman Watermen’s Museum and Talbot County Library ...
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Bay view from Calvert Cliffs, Solomons Island & State Park nearby

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

Lusby MD
Stay at this holiday home in Lusby. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Drum Point Lake and Cove Point Beach are located ...
Opens in a new windowBay view from Calvert Cliffs, Solomons Island & State Park nearby
Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes

North Beach MD
The price is NZ$541 per night from 10 May to 11 May
NZ$541
10 May - 11 May
includes taxes & fees
Stay at this family-friendly holiday home in North Beach. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Bayside History Museum and Chesapeake ...
Opens in a new windowWalk to Beach! King Bed & Free Beach Passes
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
Stay at this holiday home in Woolford. Enjoy private pools, laundry facilities and patios. Popular attractions Ragged Island and Spocott Windmill are located ...
Opens in a new window"Endless Summer" Waterfront on 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
202 Holiday Homes
Lowest Price
NZ$271
Highest Price
NZ$541
Popular accommodation
The Cozy Crab- Your Charming Haven in Lovely North Beach!, The Blue Crab Beach House - Free beach passes , "La Licorne" Waterfront Beach Cottage, 4-bedroom house w/4 Full BTH and Jacuzzi in Prince Frederick, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Bay view from Calvert Cliffs, Solomons Island & State Park nearby, Walk to Beach! King Bed & Free Beach Passes, "Endless Summer" Waterfront on the Chesapeake Bay!

Top trending hotels in St. Leonard

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 MD
Stay at this holiday home in St. Leonard. Enjoy laundry facilities, in-room fireplaces and air conditioning. Popular attractions Flag Harbor Marina and Long ...
Opens in a new window3-bedroom house in soothing Saint Leonard with AC for relaxing stays
WATERFRONT!!! The River's Roost on The Patuxent River

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

Saint Leonard MD
Stay at this holiday home in St. Leonard. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Cape Saint Marys Marina and Perigeaux Vineyards ...
Opens in a new windowWATERFRONT!!! The River's Roost on The Patuxent River
Beach Combing & Relaxation

Beach Combing & Relaxation

St Leonard MD
Stay at this holiday home in St. Leonard. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Matoaka Beach and Flag Harbor Marina are located ...
Opens in a new windowBeach Combing & Relaxation
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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$271 per night from 13 May to 14 May
NZ$271
13 May - 14 May
includes taxes & fees
Stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants and a marina. Our guests praise the helpful staff and the clean ...
Opens in a new windowRod 'N' Reel Resort
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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.