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Cottage vacation rentals in Southern Maryland

Find and book unique cottages on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Southern Maryland cottage rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Cottage rentals with a hot tub

Superhost
An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.
Cottage in Annapolis
4.84 out of 5 average rating, 89 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Guest favorite
A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.
Cottage in Saint Leonard
4.95 out of 5 average rating, 155 reviews

Block to Private Beach, Screened deck, Hot Tub

Top guest favorite
A serene water view is captured as the sun sets, casting warm hues of orange and pink across the sky. The calm surface of the water reflects the colorful clouds, while a pier extends into the scene, inviting leisure and tranquility.
Cottage in Woolford
5 out of 5 average rating, 75 reviews

Waterfront Cottage & Guesthouse Near Cambridge

Guest favorite
A covered outdoor seating area is shown, featuring a rug and a wooden table surrounded by comfortable chairs. Green trees provide shade, and a view of the calm waterfront and distant shoreline can be seen, creating a serene outdoor space for relaxation.
Cottage in Lusby
5 out of 5 average rating, 13 reviews

Riverside Haven w/ Hot Tub

Top guest favorite
A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.
Cottage in Easton
5 out of 5 average rating, 114 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Guest favorite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis
4.86 out of 5 average rating, 109 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

Top guest favorite
Cottage in Arlington
5 out of 5 average rating, 31 reviews

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

Guest favorite
A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.
Cottage in Reedville
4.89 out of 5 average rating, 216 reviews

Bay cottage 🏖on the beach. Stunning views🏝

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Pet-friendly cottage rentals

Guest favorite
Cottage in Deale
4.83 out of 5 average rating, 184 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Superhost
A remodeled cottage is set amidst a green lawn, featuring a spacious screened front porch and surrounded by trees. The building showcases a classic design with a dark exterior and a contrasting light roof, under a clear blue sky.
Cottage in Warsaw
4.91 out of 5 average rating, 127 reviews

Modern 2 Bdrm Cottage in Historic River Community

Superhost
A charming blue cottage features a spacious front deck with wooden railings and steps leading up to the entrance. Large windows allow for ample natural light, while the surrounding grass lawn and trees enhance the outdoor setting.
Cottage in Colonial Beach
4.84 out of 5 average rating, 110 reviews

Bungalow Private Beach & Dock Colonial Beach Water

Superhost
A spacious living area is presented with light-colored tile flooring, featuring a large bed with soft bedding. A dark sofa sits near a modern television, and a decorative shelving unit contrasts with the neutral walls. Natural light enhances the inviting environment.
Cottage in Alexandria
4.78 out of 5 average rating, 189 reviews

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

Guest favorite
An aerial view captures the farmhouse situated along the banks of Henry's Creek, surrounded by lush greenery. A dock extends into the water, providing access for outdoor activities. The rural landscape and nearby road are visible, emphasizing the peaceful setting.
Cottage in Kilmarnock
4.93 out of 5 average rating, 100 reviews

Creeks End Farmhouse

Top guest favorite
A dining area is presented with a modern table surrounded by white chairs, offering a casual atmosphere. Natural light pours in through large windows. A beach-themed artwork depicting a tropical scene enhances the setting, while a coffee bar is conveniently located nearby.
Cottage in North Beach
4.96 out of 5 average rating, 170 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

Superhost
A quaint yellow cottage is framed by a wooden fence and natural greenery. The front porch features colorful doors and multiple windows, allowing ample light to enter. A deck extends from the house, providing a welcoming space for relaxation amidst the surrounding trees.
Cottage in Port Republic
4.79 out of 5 average rating, 193 reviews

Shewell’s Cottage by the Shore

Guest favorite
The image captures a serene sunset over water, with a shared pier extending into the view. Silhouettes of individuals can be seen near the pier, while golden and orange hues blend with dark clouds in the sky, creating a tranquil and scenic atmosphere.
Cottage in Deal Island
4.93 out of 5 average rating, 147 reviews

Water View Cottage

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Private cottage rentals

Guest favorite
The cottage features a striking red metal roof contrasting against the greenery of the landscape. Surrounded by the water, the property includes a well-maintained lawn with trees and shrubs. The structure showcases a charming design with a welcoming entrance and outdoor steps leading to the main door.
Cottage in Lancaster
4.92 out of 5 average rating, 39 reviews

Waterfront Cottage with Beautiful Sunset Views

Guest favorite
The cottage-style home is raised on stilts, featuring a wraparound deck and large windows for expansive views of the water. The landscaped yard leads to a stone shoreline, with the serene sea stretching into the horizon under a bright blue sky.
Cottage in Lottsburg
4.98 out of 5 average rating, 94 reviews

Enchanting Edge of the World Cottage

Top guest favorite
A wooden pier extends over calm waters, leading towards a grassy area lined with trees. Rustic cottages are visible in the background, framed by lush greenery. Sunlight highlights the natural textures of the pier and the surrounding landscape.
Cottage in Tall Timbers
5 out of 5 average rating, 53 reviews

Charming Waterfront Cottage with Sunset Views

Top guest favorite
The cottage is set in a peaceful wooded area, featuring a sloping green lawn and surrounding trees. A stone pathway leads to the porch, which is bordered by a white railing. The clear blue sky and sunlight enhance the serene atmosphere.
Cottage in Hollywood
5 out of 5 average rating, 44 reviews

The Little Blue Cottage

Top guest favorite
A long wooden pier extends over the calm water, leading towards a cottage nestled amidst greenery. Surrounding land features grasses and trees, creating a natural setting. The clear blue sky enhances the sense of tranquility in this waterfront landscape.
Cottage in Piney Point
5 out of 5 average rating, 16 reviews

Beach Access | Waterfront Views | Kayaks & Bikes

Guest favorite
An outdoor seating area is set on a grassy lawn, featuring a swing structure with cozy cushions and a circular stone patio. Surrounding furniture includes two cushioned chairs and a fire pit, all framed by lush greenery, offering a serene space for relaxation.
Cottage in Lusby
4.93 out of 5 average rating, 43 reviews

Elk Cottage-Lake Lariat / Private lake access

Guest favorite
A serene view of the Chesapeake Bay stretches across the horizon, reflecting sunlight on the calm water. The beach area, featuring soft sand and gentle waves, leads up to trees dotting the shoreline. The cottage is nestled amidst the natural landscape.
Cottage in Reedville
4.91 out of 5 average rating, 53 reviews

Waterfront Bay Cottage w/ Your Own Private Beach

Top guest favorite
A serene waterfront scene is captured at sunset, featuring a private dock extending into calm waters. Vibrant colors reflect off the surface, surrounded by soft silhouettes of trees and shrubs. The sky displays hues of orange, pink, and purple, creating a tranquil atmosphere.
Cottage in Chaptico
5 out of 5 average rating, 13 reviews

Sunsets, private pier, Pax River, Leonardtown

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Destinations to explore