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Cottage vacation rentals in Southern Maryland

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Top-rated cottage rentals in Southern Maryland

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Guest favorite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

FamilyLocationHiking

4.93 out of 5 average rating, 130 reviews
Guest favorite
A wooden pier extends toward a grassy area lined with two charming cottages. The structure features sturdy wooden posts on either side, inviting guests to enjoy the tranquil view of the river and the surrounding greenery.
Cottage in Cobb Island

Happy Hour~Private dock, amazing sunsets, peaceful

Perfect for a private, scenic romantic get away or for a group of 4. Open for short- and long-stays. ‘Happy Hour’ is a uniquely furnished 2 bd/2 ba riverfront cottage at Cobb Island, Md, where you can chill to your heart’s content with panoramic views & sunsets on the Potomac River. Drop anchor! 2 bikes. Great fishing. 2 TVs, Wi-Fi, fully-equipped kitchen, W/D, deck, charming 1,100 sq.ft., 40s home. Enjoy the serenity. 3-ni. minimum reservation. Sleeps 4 max. No partiers. Unforgettable home!

LocationValueAccess

4.93 out of 5 average rating, 103 reviews
Top guest favorite
Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

ValueFamilyWifi

4.96 out of 5 average rating, 274 reviews
Top guest favorite
Cottage in Hague

Waterfront Cottage on the Potomac River

Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.

FamilyLocationTV

4.99 out of 5 average rating, 215 reviews
Top guest favorite
A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.
Cottage in California

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum featuring live concerts by top name bands.

LocationValueCondition

4.97 out of 5 average rating, 285 reviews
Top guest favorite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage

LocationFamilyCheckout

4.97 out of 5 average rating, 135 reviews
Top guest favorite
Two white Adirondack chairs are positioned on a grassy area, facing a calm water view. A stone fountain stands nearby, and a wooden dock extends into the water, offering a serene atmosphere with trees lining the shore.
Cottage in Hollywood

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". ✨

ValueLocationOutdoor spaces

4.99 out of 5 average rating, 107 reviews
Top guest favorite
The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.
Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

Original waterfront cottage in North Beach is perfect for a small family or two couples. Beautiful sunrises and moonrises over the boardwalk from the front deck. Walk to restaurants and nightlife, stroll the boardwalk, chill on the beach or go to the spa or charter fishing in Chesapeake Beach. Pet friendly. Beach Passes, umbrella and chairs included. 2 bedrooms plus a twin daybed that pulls out to queen bed.

LocationValueBathroom

4.95 out of 5 average rating, 107 reviews
Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

FamilyValueDecor

4.96 out of 5 average rating, 182 reviews
Guest favorite
The cottage is framed by a large flowering tree and surrounded by lush greenery. A spacious screened porch is visible in front, providing a cozy outdoor space. Daffodils bloom in the foreground, enhancing the rural setting on a peaceful landscape.
Cottage in Lottsburg

Charming Waterfront Home with Expansive Views

Mom and Pop's Honest Point Home has been in our family for almost 70 years. It has been and continues to be a haven for anyone seeking a relaxing rural property. The cottage is situated on many acres surrounded by water, farmland and wildlife. Your only neighbor is the owner's home which is next door. Make sure you read the details below

FamilyLocationAir conditioning

4.92 out of 5 average rating, 119 reviews
Top guest favorite
Cottage in Montross

Waterfront Cottage | Private Dock + Water Toys

Relax on the water at Mallard Cottage, a peaceful retreat on beautiful Nomini Creek. Spend your days swimming, fishing, kayaking, and paddleboarding right from the private dock. With four decks, plenty of outdoor space, and everything you need for a comfortable getaway, it's an easy place to slow down and enjoy time together.

FamilyValueCheckout

4.99 out of 5 average rating, 223 reviews
Top guest favorite
The cottage exterior showcases charming blue shingles and a welcoming front porch, furnished with a bench and four chairs. A spacious deck offers outdoor seating and is surrounded by lush greenery and flower beds, enhancing the warm ambiance of the property.
Cottage in Tracys Landing

Charming Waterfront on Chesapeake Bay

Perched on a bank overlooking expansive views of the Chesapeake Bay, our shingled cottage is a comfortable country retreat with exposed beams and cathedral ceilings. It is less than an hour to Annapolis and Washington DC. Save on your first Airbnb stay (some restrictions apply): https://abnb.me/e/i9PHYamHUN

FamilyValueIndoor spaces

4.9 out of 5 average rating, 405 reviews

Popular amenities for Southern Maryland cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Guest favorite
Cottage in Deale

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

LocationValueAccuracy

4.83 out of 5 average rating, 201 reviews
Guest favorite
A spacious yard features a hammock suspended between two trees, overlooking the bay. Colorful Adirondack chairs are positioned nearby, creating an inviting spot for relaxation. The calm water stretches into the distance under a clear sky, providing a serene atmosphere.
Cottage in Reedville

Private point on the Bayhammock, hot tub, kayaks

ValueLocationAir conditioning

4.88 out of 5 average rating, 261 reviews
Guest favorite
Cottage in Heathsville

Waterfront Cottage w Water Access, Sauna, Hot Tub

FamilyLocationCleanliness

4.93 out of 5 average rating, 148 reviews
Top guest favorite
Cottage in North Beach

Waterfront Cottage Near Herrington and North Beach

FamilyLocationWalkability

4.97 out of 5 average rating, 381 reviews
Top 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

Riverside Haven w/ Hot Tub

LocationFamilyHiking

4.97 out of 5 average rating, 86 reviews
Guest favorite
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby

Hot Tub Hideaway by Shark Tooth Shores

FamilyLocationComfort

4.85 out of 5 average rating, 98 reviews
Superhost
A serene waterfront property is displayed, featuring a two-story structure with a spacious deck overlooking the sandy beach. The outdoor area includes lounge chairs and a nearby kayaks, all framed by calm waters and lush greenery in the background.
Cottage in Scotland

Hays Beach House - Hot Tub - Private Beach

LocationFamilyParks

4.79 out of 5 average rating, 24 reviews
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

Bay Cottage w/ Pier-Kayaks near Cambridge

ValueFamilyBreakfast

5.0 out of 5 average rating, 90 reviews

Pet-friendly cottage rentals

Top guest favorite
The charming beach house features a white picket fence and a welcoming front porch. A large anchor motif is displayed prominently above the door. Surrounding greenery provides a natural backdrop, enhancing the cozy exterior aesthetics in a tranquil setting.
Cottage in Lusby

Gettin to the point. ( Cove Point Beach)

LocationFamilyAir conditioning

4.98 out of 5 average rating, 301 reviews
Top guest favorite
A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.
Cottage in Reedville

"Dragonfly" Waterfront Cottage on Chesapeake Bay

FamilyValueBeach

4.91 out of 5 average rating, 233 reviews
Guest favorite
The exterior of a two-story cottage is shown, featuring a blue metal roof and white siding. Blue shutters frame the windows. A small deck is visible in front, furnished with two adirondack chairs in bright green. A door centrally accesses the home.
Cottage in Wingate

Blue Crab Cottage: Remote+Nature+Fishing+Views

FamilyValueWalkability

4.84 out of 5 average rating, 100 reviews
Guest favorite
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

Modern 2 Bdrm Cottage in Historic River Community

FamilyLocationAccess

4.92 out of 5 average rating, 141 reviews
Top guest favorite
A serene waterfront scene is framed by a sprawling tree. Boats are moored along the docks, with calm water reflecting the sky. Quaint buildings line the shore, and a bench is positioned on the grass, inviting quiet contemplation of the picturesque surroundings.
Cottage in St. Michaels

The Little Anchor Cottage, St. Michaels, MD

LocationFamilyPool

4.97 out of 5 average rating, 301 reviews
Guest favorite
The exterior of the cottage features a welcoming wooden porch with a railing, flanked by two chairs. The fully fenced yard is surrounded by lush greenery, and a well-maintained pathway leads to the front steps. Soft lighting enhances the entrance, creating an inviting ambiance.
Cottage in Colonial Beach

Colonial Beach Cottage, 7 minutes walk to beach!

FamilyValueWifi

4.91 out of 5 average rating, 114 reviews
Top guest favorite
The exterior of the guest house is showcased, featuring a unique angled roof and large windows that invite natural light. Surrounding greenery includes shrubs and small trees, enhancing the home’s connection to nature. A circular window adds a distinctive architectural detail.
Cottage in Del Ray

Great guest house —Del Ray, Alexandria, VA

FamilyLocationAmenities

4.93 out of 5 average rating, 104 reviews
Top guest favorite
A cottage is set within a private wooded yard, surrounded by lush greenery. The exterior features white siding and black shutters. A grassy area leads to a wooden porch with steps, while a seating area is visible in the garden, offering a peaceful retreat.
Cottage in Cambridge

Cambridge Cottage

ValueFamilyHospitality

4.98 out of 5 average rating, 121 reviews

Private cottage rentals

Guest favorite
A charming cottage exterior is framed by lush greenery and tress, featuring yellow shutters that accentuate the white façade. A path of stepping stones leads to the inviting front door, while a glimpse of water is visible in the background.
Cottage in Leonardtown

Potomac River Freedom Cottage

LocationValueView

4.91 out of 5 average rating, 254 reviews
Top guest favorite
A warm living area features a brown leather sofa adorned with decorative pillows. A round ottoman adds a pop of color, while a textured area rug anchors the space. Natural light filters through green curtains, complemented by stylish lighting fixtures and wall artwork.
Cottage in Heathsville

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

FamilyLocationBathroom

4.94 out of 5 average rating, 266 reviews
Top guest favorite
An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.
Cottage in Heathsville

Cottage with a view!

FamilyValueBiking

4.89 out of 5 average rating, 136 reviews
Guest favorite
A charming cottage exterior showcases a well-maintained garden with colorful flowers lining the pathway. The front porch features a welcoming entrance, while large windows provide ample natural light. A white picket fence frames the lush greenery that surrounds the home.
Cottage in North Beach

Quiet Coastal Cottage Escape with Water Views

LocationValueDecor

4.91 out of 5 average rating, 130 reviews
Top guest favorite
A serene view of a shared pier extending into calm waters, showcasing several boats docked. The still water reflects the cloudy sky and surrounding greenery, creating a tranquil atmosphere. Vertical posts line the pier, enhancing the waterfront experience.
Cottage in Colonial Beach

Sunset Point-Waterfront home&shared pier for boat!

FamilyLocationOutdoor spaces

4.93 out of 5 average rating, 107 reviews
Guest favorite
A sandy beach borders calm waters, reflecting sunlight under a bright blue sky filled with clouds. Dark rocks and a grassy area play a role in the natural landscape, while distant structures along the shore suggest waterfront access.
Cottage in Reedville

Chesapeake Bay Beach Cottage

LocationFamilyKitchen

4.91 out of 5 average rating, 235 reviews
Guest favorite
The exterior of a charming beach cottage is visible, featuring a sloped roof and multiple windows. A green street sign indicates the intersection of Chesapeake Avenue and 7th Street. Lush green grass and shrubs surround the property's fence.
Cottage in North Beach

Full house rental in Twin Beach. 1 bk from the Bay

LocationFamilyOutdoor spaces

4.87 out of 5 average rating, 198 reviews
Superhost
Cottage in Reedville

Bull Neck Cottage

ValueFamilyHeating

4.93 out of 5 average rating, 161 reviews

Destinations to explore