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Browse Select St. Leonard Cottages

Family-friendly Chesapeake Beach House With Deck!
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, coffee grinder
Family-friendly Chesapeake Beach House With Deck!
3.0 star property
6.0 out of 10, (1)
Family-friendly Chesapeake Beach House With Deck!
Updated North Beach Cottage: Pet Friendly!
Exterior
Updated North Beach Cottage: Pet Friendly!
3.0 star property
Updated North Beach Cottage: Pet Friendly!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
3.0 star property
10.0 out of 10, Exceptional, (1)
"It really is an adorable cottage, very tastefully decorated.the owner provided a very thoughtful gift basket on arrival. I would recommend this cottage to anyone."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront Rock Point Vacation Rental w/ Sunroom!
Property grounds
Waterfront Rock Point Vacation Rental w/ Sunroom!
3.0 star property
2.0 out of 10, (1)
"Absolutely the grossest property I've been too. 5 spiders, 1 centipede, 1 dead cockroach. Master bedroom and bathroom both had see through curtains so people could look through. Hair in the sink and wads of hair stuck to the bathroom hinge. Window AC units had gaps in them so bugs could come in without hindrance. Leaves in the ac ducts(how). Couldn’t even cut the grass for before guest arrive. We didn't even stay there. "
Waterfront Rock Point Vacation Rental w/ Sunroom!
Riverside House w/ Kayaks, Piano & Fireplace
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Riverside House w/ Kayaks, Piano & Fireplace
3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Waterfront Cottage in Piney Point w/ Kayaks!
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Waterfront Cottage in Piney Point w/ Kayaks!
3.0 star property
Waterfront Cottage in Piney Point w/ Kayaks!
Waterfront North Beach Home ~ 2 Mi to Beach!
Exterior
Waterfront North Beach Home ~ 2 Mi to Beach!
3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
Tranquil Port Republic Home w/ Water Views!
Interior
Tranquil Port Republic Home w/ Water Views!
3.0 star property
Tranquil Port Republic Home w/ Water Views!
Bayfront Gem w/ Amazing Water Views + Pond!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Bayfront Gem w/ Amazing Water Views + Pond!
3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
Pet-friendly Home: Spacious Yard + Community Perks
House (5 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Pet-friendly Home: Spacious Yard + Community Perks
3.0 star property
Pet-friendly Home: Spacious Yard + Community Perks
Riverfront Newburg Cottage w/ Deck & Gas Grill!
Cottage (3 Bedrooms) | Private kitchen | Coffee/tea maker, paper towels
Riverfront Newburg Cottage w/ Deck & Gas Grill!
3.0 star property
Riverfront Newburg Cottage w/ Deck & Gas Grill!
Waterfront House With Dock, Kayaks, & Sailboat!
Interior
Waterfront House With Dock, Kayaks, & Sailboat!
3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Maryland Vacation Rental: Walk to Beach
Interior
Maryland Vacation Rental: Walk to Beach
3.0 star property
Maryland Vacation Rental: Walk to Beach
North Beach Cottage - Walk to Chesapeake Bay
Interior
North Beach Cottage - Walk to Chesapeake Bay
3.0 star property
North Beach Cottage - Walk to Chesapeake Bay
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
House (Multiple Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Interior
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
3.0 star property
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Interior
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
3.0 star property
Waterfront Lusby Escape w/ Fire Pit & Kayaks!
Maryland Vacation Rental w/ Private Pool & Dock
Terrace/patio
Maryland Vacation Rental w/ Private Pool & Dock
3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock
Modern Solomons Cottage Rental - Walk to Island!
Interior
Modern Solomons Cottage Rental - Walk to Island!
3.0 star property
Modern Solomons Cottage Rental - Walk to Island!
Waterfront Taylors Island Rental w/ Private Dock!
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Waterfront Taylors Island Rental w/ Private Dock!
3.0 star property
Waterfront Taylors Island Rental w/ Private Dock!
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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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Frequently asked questions

How much do cottages in St. Leonard cost?
You can expect to pay between and per night for cottages in St. Leonard. Whatever your budget, a terrific stay is only clicks away on Expedia. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in St. Leonard with Expedia?
We think that vacays should be hassle-free, so if you’re chasing cottages in St. Leonard at an affordable rate, Expedia has your back. Keep the budget under control and select a wallet-friendly option surrounded by nature, or book an upmarket cottage to pamper your loved ones.
How can I find cheap cottages in St. Leonard?
The quickest way to uncover cheap cottages in St. Leonard is with Expedia’s convenient filter tool. Fine-tune your search results by budget, amenities and star rating to secure awesome rates with only a few clicks.
What is there to do in St. Leonard near my cottage?
If you’re ready to fill up your itinerary in St. Leonard, don’t miss Jefferson Patterson Park and Museum. It’s a hit with locals and travellers alike.