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Cottage vacation rentals in Southern Maryland

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Top-rated cottage rentals in Southern Maryland

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Guest favorite
A cozy living area features a brown leather sofa adorned with patterned throw pillows. A round, orange accent stool is positioned next to a low coffee table, which holds a decorative tray. A woven rug covers the polished wooden floor, and greenery adds a touch of nature.
Cottage in Heathsville
4.93 out of 5 average rating, 237 reviews

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

We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

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
4.9 out of 5 average rating, 115 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

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
4.98 out of 5 average rating, 283 reviews

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

Guest favorite
A charming white cottage presents a welcoming facade, featuring a covered porch with two light blue chairs and a small table. A well-maintained lawn with green grass and a landscaped border is visible, while a white picket fence enhances the front yard.
Cottage in North Beach
4.95 out of 5 average rating, 172 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Guest favorite
A charming cottage sits at the water's edge, surrounded by lush greenery. A wooden staircase leads down from an elevated deck to the sandy beach. Two blue chairs are positioned on the deck, inviting relaxation as the sun sets in the background.
Cottage in Leonardtown
4.96 out of 5 average rating, 229 reviews

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.

Top guest favorite
Cottage in Saint Leonard
4.96 out of 5 average rating, 167 reviews

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Fall/Winter promo: Book two nights, get one free on midweek stays (Monday thru Thursday)! Book two nights, get 50% off third night on weekend stays. Send a message after booking, and the promo night will be added. Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) Message for multi-night and monthly rates.

Top guest favorite
A wooden dock extends into the calm water, surrounded by lush greenery along the shoreline. The scene showcases a tranquil landscape with a gradual sandy area visible at low tide, framed by a clear blue sky dotted with fluffy white clouds.
Cottage in Heathsville
4.92 out of 5 average rating, 130 reviews

Waterfront Cottage w Hot Tub, Kayak, Fishing

Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, take a dip in the hot tub, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

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
4.91 out of 5 average rating, 212 reviews

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

Top guest favorite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in Saint Michaels
4.97 out of 5 average rating, 176 reviews

La Casita on Harris Creek, St. Michaels

Newly constructed architecturally unique guesthouse inspired by the historic barns of the Chesapeake. Stay in luxury on a secluded 40 acre farm on Harris Creek, be at one with nature & still only 5 min from town's fine dining, shops & charm . With 360 views, TV/Wi-fi, full bath/shower, galley kitchen w/ microwave, fridge w/ice maker, washer/drier, patio fire pit, private pool & kayaks. We comply with Talbot County's zoning that requires a 3 night minimum ST-934-HUD 2020.

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
4.97 out of 5 average rating, 256 reviews

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.

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
4.96 out of 5 average rating, 114 reviews

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

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
4.92 out of 5 average rating, 235 reviews

Potomac River Freedom Cottage

Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). **Off-season long term rentals available with washer/dryer access, please contact me to discuss

Popular amenities for Southern Maryland cottage rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a 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, 80 reviews

Waterfront Cottage & Guesthouse w/Hot Tub

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
4.97 out of 5 average rating, 34 reviews

Riverside Haven w/ Hot Tub

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
4.88 out of 5 average rating, 234 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

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, 118 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Top guest favorite
Cottage in Arlington
5 out of 5 average rating, 47 reviews

Luxury Cottage | Hot Tub & Quiet Oasis Near DC

A furnished deck is surrounded by greenery, featuring a dining set under a large umbrella. Comfortable seating and a patterned area rug enhance the space, with details such as a small decorative lantern and a heating lamp visible.
Cottage in Chesapeake Beach
4.54 out of 5 average rating, 26 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

Top 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
4.94 out of 5 average rating, 108 reviews

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

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
4.78 out of 5 average rating, 64 reviews

Hot Tub Hideaway by Shark Tooth Shores

Pet-friendly cottage rentals

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 Saint Michaels
4.97 out of 5 average rating, 260 reviews

The Little Anchor Cottage, St. Michaels, MD

Guest favorite
Cottage in Fredericksburg
4.91 out of 5 average rating, 151 reviews

“Little Sligo” Historic Downtown Cottage Near I-95

Guest favorite
A shaded outdoor area features a glass-top dining table surrounded by six chairs, situated on lush green grass. Nearby, additional loungers invite relaxation, under the canopy of a large tree with vibrant foliage, overlooking a calm waterfront view.
Cottage in Deale
4.82 out of 5 average rating, 186 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

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
4.92 out of 5 average rating, 132 reviews

Modern 2 Bdrm Cottage in Historic River Community

Top guest favorite
The exterior of a single-story cottage is framed by lush greenery and mature trees. A white picket fence encloses the front yard, which features a small lawn and a decorative tree. Gravel pathways lead to the front entrance, with a shaded area beside the house.
Cottage in Deale
4.91 out of 5 average rating, 175 reviews

Rockhold Creek Cottage

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, 120 reviews

Bungalow Private Beach & Dock Colonial Beach Water

Guest favorite
The living area features vaulted ceilings with exposed beams and skylights allowing natural light to fill the space. A combination of orange and blue furnishings, including a spacious sofa and accent chairs, surround a coffee table. Decorative elements and a large area rug add warmth to the room.
Cottage in Neavitt
4.87 out of 5 average rating, 151 reviews

The Middle Point Cottage at Saint Michaels

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
4.91 out of 5 average rating, 112 reviews

Charming Waterfront Home with Expansive Views

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
4.93 out of 5 average rating, 40 reviews

Waterfront Cottage with Beautiful Sunset Views

Guest favorite
A cozy living area features a brown leather sofa and an armchair, both adorned with decorative pillows. A woven coffee table sits in the center, while a side table with a lamp provides soft lighting. Natural light filters in through large windows, enhancing the warm ambiance.
Cottage in Reedville
4.87 out of 5 average rating, 63 reviews

Bayberry - awesome Solo Stove Fire Pit

Guest favorite
A spacious living area features a light-colored sofa and a brown sectional couch adorned with decorative pillows. A round coffee table sits in front of the seating. Views of the dining area are visible, showcasing a wooden table surrounded by chairs and large windows letting in natural light.
Cottage in Colonial Beach
4.95 out of 5 average rating, 19 reviews

Available Winter Festival Parade*firepit*grill

Guest favorite
A charming one-bedroom cottage is attached to a historic home, featuring a blue shingle roof and light green exterior. Lush shrubs and neatly trimmed bushes frame the entrance, which is highlighted by a welcoming front door and outdoor lighting.
Cottage in Alexandria
4.92 out of 5 average rating, 26 reviews

The Colonial Cottage of Alexandria

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, 97 reviews

Enchanting Edge of the World Cottage

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 Alexandria
4.91 out of 5 average rating, 81 reviews

Great guest house —Del Ray, Alexandria, VA

Top guest favorite
An open living space features a modern kitchen with stainless steel appliances and white cabinetry. A wooden dining table with light-colored chairs is positioned centrally, accompanied by a cozy seating area. Large windows provide natural light and a view of the adjoining four-season porch.
Cottage in Montross
4.98 out of 5 average rating, 51 reviews

Harbor Cottage

Top guest favorite
The exterior of the cottage is showcased, featuring a charming green facade with white trim. A spacious front porch with large windows invites guests to enjoy the surrounding landscape. A large tree is visible above the cottage, enhancing the picturesque setting.
Cottage in Kinsale
5 out of 5 average rating, 41 reviews

River + Beach Front Cottage 4 BR ADA Northern Neck

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