Search Cottages in Southern Maryland

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Compare 34 Cottages in Southern Maryland with updated reviews, rates, and availability.

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!
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Shower

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Beachy Maryland A-frame: Steps to Chesapeake Bay!
Interior

Beachy Maryland A-frame: Steps to Chesapeake Bay!

3.0 star property
Beachy Maryland A-frame: Steps to Chesapeake Bay!
Cottage w/ Potomac River Views in Newburg!
Cottage (3 Bedrooms) | Interior

Cottage w/ Potomac River Views in Newburg!

3.0 star property
Cottage w/ Potomac River Views in Newburg!
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
Beach towels

Maryland Vacation Rental: Walk to Beach

3.0 star property
Maryland Vacation Rental: Walk to Beach
North Beach Cottage - Walk to Chesapeake Bay
Game room

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
North Beach Cottage - Walk to Chesapeake Bay
Waterfront Lusby Retreat w/ Deep-water Dock & Slip
Beach towels

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!
TV, books

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
Outdoor dining

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!
View from property

Modern Solomons Cottage Rental - Walk to Island!

3.0 star property
Modern Solomons Cottage Rental - Walk to Island!
Sunrise Views: Waterfront Lusby Home w/ Deck!
Property grounds

Sunrise Views: Waterfront Lusby Home w/ Deck!

3.0 star property
Sunrise Views: Waterfront Lusby Home w/ Deck!
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
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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Other property types in Southern Maryland

Frequently asked questions

How much do cottages in Southern Maryland cost?
Expect to pay between and per night for cottages in Southern Maryland. No matter your budget, a fantastic stay is only a few clicks away on Expedia. These prices were 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.
How many cottages are there in Southern Maryland?
Explore our 34 cottages in Southern Maryland and reserve your favorite. Whether you’re thinking about a family vacay or a break with friends, your perfect stay is just clicks away with Expedia.
Why book your cottage in Southern Maryland with Expedia?
Reserving a cottage in Southern Maryland is as easy as clicking on your travel dates and picking your ideal place for a getaway in nature. From luxurious retreats to low-cost stays and cottages that include perks like free WiFi, Expedia has something for all styles. As for terrific deals? We’ve got your back!
How can I find cheap cottages in Southern Maryland?
An excellent way to uncover cheap cottages in Southern Maryland is with Expedia’s useful filter tool. Tailor your search results by budget, amenities and star rating to land awesome bargains in just a few keystrokes.
What is there to do in Southern Maryland near my cottage?
No matter your interests, there are tons of things to put on your to-do list in Southern Maryland. If you’re headed to Bowie, don’t miss Prince George’s Stadium, Belair Mansion and Allen Pond Park. Planning an escape in La Plata? Port Tobacco Players, Hawthorne Country Club and College of Southern Maryland are among the top sights here.