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Cottages in Southern Maryland

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Relax in a spacious living area with a sofa, coffee table, and wicker basket, featuring a kitchen with stainless steel appliances and a granite countertop.

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!
Relax under a thatched umbrella in a serene outdoor setting surrounded by lush greenery.

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!
Relax on the deck with a clear view of the water, surrounded by a tranquil atmosphere.

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!
Charming single-story home with a front porch and garden area, surrounded by a fence and trees.

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!
Enjoy a meal by the water with a scenic view from the outdoor dining area, featuring a hammock and a pier.

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!
House (2 Bedrooms) | 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
Cottage (3 Bedrooms) | Interior

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!
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, and 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!
Walk to Beach: Charming Maryland Home w/ Yard!
Enjoy a serene beach experience with access to calm waters and a picturesque jetty.

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!
Riverside House w/ Kayaks, Piano & Fireplace
Enjoy cooking in the well-equipped kitchen with a central island, sink, and ample counter space, complemented by a large window.

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Beachy Maryland A-frame: Steps to Chesapeake Bay!
House (3 Bedrooms) | 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
Enjoy outdoor dining and socializing in this serene garden setting, complete with a covered deck and comfortable seating.

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!
Enjoy dining in this stylish space with a large round table, comfortable chairs, and a flat-screen TV.

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
House (5 Bedrooms) | 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!
Cottage (1 Bedroom) | Interior

Dock Access: Waterfront Cottage in Avenue!

3.0 star property
Dock Access: Waterfront Cottage in Avenue!
Sunrise Views: Waterfront Lusby Home w/ Deck!
House (4 Bedrooms) | 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
House (4 Bedrooms) | 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!
Relax on the deck with a table and two chairs, surrounded by lush greenery and a serene view.

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!
Enjoy a serene view of the lush landscape from this room's window, featuring a table with a vase, candle, and tray.

Waterfront House With Dock, Kayaks, & Sailboat!

3.0 star property
Waterfront House With Dock, Kayaks, & Sailboat!
Waterfront Leonardtown Retreat w/ Dock Access!
Relax on the porch with a view of the water and shoreline.

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.
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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 41 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.