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Vacation rentals in Saint Leonard

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Top-rated vacation rentals in Saint Leonard

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cottage in Saint Leonard
Block to Beach! Hot Tub, Water View, Coffee Bar
Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach) There are 2 bedrooms, 1.5 baths, full kitchen stocked with essentials, laundry on site, gas bbq, fully stocked coffee bar (Keurig and standard drip) and a fire pit! Check out my guidebook for outing ideas and restaurants! (No cleaning fee and multi night discounts!)
$190 per night
Home in Saint Leonard
Charming Cottage by the Chesapeake Bay
The Dragonfly Cottage! Relax in this calm, stylish space on the Chesapeake Bay, ONE block from a private community Calvert Beach. Enjoy walking along the beach finding shells, shark teeth, and even fossils! Drive to the Flag Harbor Marina, Solomon's Island, Flag Pond Nature Preserve, and Calvert Cliffs State Park. Saint Leonard is driving distance to Annapolis, Baltimore, and Washington, DC. There's even a park ride access. Sorry, NO animals what so ever due to owner's severe allergies!
$139 per night
Guesthouse in Saint Leonard
Studio on the Bay.
This studio apartment is in walking distance to three private beaches in our community. There is 1 bedroom with a queen size bed, spacious bathroom and closet. The living room has a pull out full size bed and a kitchenette. Coffee, teas, beach chairs, cooler, fishing poles and tackle are provided. Being on the western shore provides amazing sunrises and lots of hiking nearby. Fifteen minutes from Solomons Island (home of the Tiki Bar). An hour or so from DC, Annapolis and Waldorf.
$126 per night

Stay near Saint Leonard's top sights

Photo of Matoaka Beach Cabins
Matoaka Beach Cabins4 locals recommend
Photo of The Tavern
The Tavern6 locals recommend
Photo of Happy Buddha
Happy Buddha4 locals recommend
Photo of Chesapeake Market Place
Chesapeake Market Place11 locals recommend
Photo of St Leonard Volunteer Fire Co
St Leonard Volunteer Fire Co3 locals recommend
Photo of ATM Machine at The Tavern
ATM Machine at The Tavern4 locals recommend

Other great vacation rentals in Saint Leonard

Home in Saint Leonard
Hickory House on the Chesapeake Bay!
$147 per night
Rental unit in Port Republic
Serenity Suite on Chesapeake Bay
$124 per night
Guest suite in Saint Leonard
Shewell’s Basement Studio at Long Beach
$38 per night
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
$163 per night
Private room in Port Republic
Bayview at Hilltop
$71 per night
Cottage in Saint Leonard
Captain Jack's Bay Hideaway
$150 per night
Rental unit in Port Republic
Bayview Apartment with a private entrance.
$99 per night
Cottage in Saint Leonard
Cozy Cedar Cottage Chesapeake Bay
$121 per night
Cottage in Port Republic
Shewell’s Cottage by the Shore
$184 per night
Home in Saint Leonard
Cozy Beach House Chesapeake Bay Getaway
$137 per night
Rental unit in Lusby
Nice view self-contained Apart.
$65 per night
Private room in Saint Leonard
Private Bedroom 1.5 blocks from the Bay
$65 per night
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