Search Cottages in Southern Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

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!
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!
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!
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!
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
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!
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!
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!
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
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!
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!
Sunrise Views: Waterfront Lusby Home w/ Deck!
Front of property

Sunrise Views: Waterfront Lusby Home w/ Deck!

3.0 star property
Sunrise Views: Waterfront Lusby Home w/ Deck!
Maryland Vacation Rental w/ Private Pool & Dock
Interior

Maryland Vacation Rental w/ Private Pool & Dock

3.0 star property
Maryland Vacation Rental w/ Private Pool & Dock
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!
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!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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.