Search Cottages in Southern Maryland

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Featured Cottages in Southern Maryland

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Interior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very Good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Waterfront North Beach Home ~ 2 Mi to Beach!
Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!
North Beach Cottage - Walk to Chesapeake Bay
Game room

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay
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!
Private kitchen

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!
Riverside House w/ Kayaks, Piano & Fireplace
Private kitchen

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
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 Rock Point Vacation Rental w/ Sunroom!
Interior

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!
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Outdoor dining

Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit

3.0 star property
Secluded Lothian Farmhouse on 45 Acres w/ Fire Pit
Pet-friendly Maryland Home on the Potomac River!
Interior

Pet-friendly Maryland Home on the Potomac River!

3.0 star property
8.0 out of 10, Very Good, (1)
"Quiet. Porch right on water nice. Clean."
Pet-friendly Maryland Home on the Potomac River!
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
Dock Access: Waterfront Cottage in Avenue!
Interior

Dock Access: Waterfront Cottage in Avenue!

3.0 star property
Dock Access: Waterfront Cottage in Avenue!
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!
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!
Screened Patio, Deck & Grill: Saint Inigoes Home!
Interior

Screened Patio, Deck & Grill: Saint Inigoes Home!

3.0 star property
Screened Patio, Deck & Grill: Saint Inigoes Home!
Modern Solomons Cottage Rental - Walk to Island!
1 bedroom, iron/ironing board, bed sheets

Modern Solomons Cottage Rental - Walk to Island!

3.0 star property
Modern Solomons Cottage Rental - Walk to Island!
Cottage w/ Potomac River Views in Newburg!
Interior

Cottage w/ Potomac River Views in Newburg!

3.0 star property
Cottage w/ Potomac River Views in Newburg!
Walk to Beach: Charming Maryland Home w/ Yard!
Interior

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
Walk to Beach: Charming Maryland Home w/ Yard!
Cottage on the Potomac in Newburg: Shared Pier!
Interior

Cottage on the Potomac in Newburg: Shared Pier!

3.0 star property
Cottage on the Potomac in Newburg: Shared Pier!
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 Southern Maryland cost?
Cottages in Southern Maryland range between and per night. These stays offer a chance to get in touch with nature --- at a price you can afford. 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?
Southern Maryland has 42 cottages to choose from. Enter your destination and travel dates and lock in your next escape today.
Why book your cottage in Southern Maryland with Expedia?
Expedia has some excellent cottages in Southern Maryland, so get ready for a memorable stay close to nature. If you need to stick to a budget, choose how much you'd like to spend and the star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right digs whatever your bank balance or plans.