Search Cottages in Southern Maryland

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Feb 28 - Mar 2
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Apr 18 - Apr 20

Compare 37 Cottages in Southern Maryland with updated reviews, rates, and availability.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

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
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!
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
6.0 out of 10, (1)
"The property needs a severe cleaning. The floors were filthy. "
Updated North Beach Cottage: Pet Friendly!
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!
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!
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!
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!
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!
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
Maryland Vacation Rental: Walk to Beach
Beach towels

Maryland Vacation Rental: Walk to Beach

3.0 star property
Maryland Vacation Rental: Walk to Beach
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Exterior

Bayfront Maryland Retreat w/ Deck, Near Beaches!

3.0 star property
Bayfront Maryland Retreat w/ Deck, Near Beaches!
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
Walk to Beach: Pet-friendly Gem in Scotland!
Interior

Walk to Beach: Pet-friendly Gem in Scotland!

3.0 star property
Walk to Beach: Pet-friendly Gem in Scotland!
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
TV

Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!

3.0 star property
Lakefront Lusby Home w/ Fire Pit: 3 Mi to Beach!
Waterfront House With Dock, Kayaks, & Sailboat!
Interior

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Waterfront Leonardtown Retreat w/ Dock Access!
Terrace/patio

Waterfront Leonardtown Retreat w/ Dock Access!

3.0 star property
Waterfront Leonardtown Retreat w/ Dock Access!
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
Water-view Deale Home: Walk to Marina, Restaurants
Interior

Water-view Deale Home: Walk to Marina, Restaurants

3.0 star property
Water-view Deale Home: Walk to Marina, Restaurants
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 37 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.