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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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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, 280 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.

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, 215 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.

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

4.93 out of 5 average rating, 122 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!

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, 173 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 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, 113 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

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, 245 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, 109 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

Top guest favorite

The view from the deck features lush trees framing a sandy beach and the calm waters of the Potomac River. Two stylish planters filled with yellow flowers are positioned at the entrance, adding a pop of color to the serene landscape.

Cottage in Hague

4.99 out of 5 average rating, 169 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

The exterior of the cottage features a welcoming red door framed by white clapboard siding and black shutters. Flower pots with pink blooms are hung on either side, adding a touch of color. A set of steps leads up to the entrance, surrounded by green foliage.

Cottage in Fredericksburg

4.86 out of 5 average rating, 469 reviews

Rappahannock River Cottage Near I-95 Sleeps 6!

Charming 3-Bedroom with rustic charm Built in 1895. Ideal location for shopping, entertainment, history, and outdoor adventures. Discover all things Fredericksburg! Your cozy haven awaits! 🏡✨ New for 2025!! —Updated hardwood flooring throughout the whole house. Also, a small fenced in front yard (3 1/2 foot tall) AND screened in front door complete with doggie door for the fur babies! 🐕 🐾

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

4.95 out of 5 average rating, 167 reviews

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.

Top guest favorite

An outdoor deck features comfortable seating with two rocking chairs and an outdoor sofa, arranged around a propane fire pit. A vibrant orange umbrella provides shade, overlooking the tranquil water of Nomini Creek, with lush greenery and a private dock in the background.

Cottage in Montross

4.98 out of 5 average rating, 180 reviews

Newly Renovated 2BR Waterfront Cottage with Dock

Escape to Mallard Cottage, our newly renovated home nestled along the picturesque Nomini Creek. Step onto the private dock for direct water access, where you can launch one of our paddleboards or kayaks for a day of exploration. Highlights include: ✔ 4 Outdoor Decks ✔ High-Speed Wi-Fi ✔ Central Heating & Air Conditioning ✔ Game Room ✔ Free Parking ✔ No Cleaning Fee!

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, 111 reviews

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

Vacation rentals for every style

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Cabins

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A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Southern Maryland cottage rentals

Free parking on premises

Air 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, 75 reviews

Waterfront Cottage & Guesthouse Near Cambridge

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, 12 reviews

Riverside Haven w/ Hot Tub

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, 220 reviews

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

Top guest favorite

A spacious outdoor deck is furnished with a sectional sofa arranged around a central table. Soft lighting from string lights enhances the atmosphere. In the corner, a hot tub is positioned, surrounded by nature and trees that create a serene backdrop.

Cottage in Lusby

5 out of 5 average rating, 22 reviews

Cozy Cottage close to Beaches & Solomon’s Island

Top guest favorite

Cottage in Arlington

5 out of 5 average rating, 31 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

4.6 out of 5 average rating, 25 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

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

4.93 out of 5 average rating, 100 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

4.76 out of 5 average rating, 55 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

4.98 out of 5 average rating, 247 reviews

The Little Anchor Cottage, St. Michaels, MD

A charming cottage is framed by lush greenery and a manicured lawn. Sunlight filters through the leaves overhead, highlighting the exterior, which features light-colored siding and flower beds. A small porch on the side invites guests to enjoy the tranquil outdoor setting.

Cottage in Fredericksburg

4.92 out of 5 average rating, 134 reviews

“Little Sligo” Historic Downtown Cottage Near I-95

A bright living area features an orange couch complemented by blue and grey accent chairs. A circular coffee table sits on a patterned rug, surrounded by large windows that provide ample natural light, highlighting the beautiful hardwood flooring. A well-equipped kitchen is visible in the background.

Cottage in Arlington

4.8 out of 5 average rating, 269 reviews

Clarendon: Metro Dog-friendly 40" Roku Park Patio

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

Cottage in Deale

4.83 out of 5 average rating, 184 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

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

4.85 out of 5 average rating, 106 reviews

Bungalow Private Beach & Dock Colonial Beach Water

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!!!

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*

Private cottage rentals

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

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

4.95 out of 5 average rating, 97 reviews

Happy Hour~Private dock, amazing sunsets, peaceful

The image captures a serene waterfront scene at sunset, highlighting a calm expanse of water with a private dock extending into the bay. Soft hues of orange and pink reflect on the surface, while stone-lined shores frame the picturesque view.

Cottage in Piney Point

4.96 out of 5 average rating, 49 reviews

Quaint fishing retreat on the lower Potomac Piney

A serene waterfront scene showcases a private dock extending into the water, framed by grassy areas. The horizon is painted with purple and orange hues from the setting sun, reflecting on the water's surface. Trees line the backdrop, adding to the tranquil atmosphere.

Cottage in Cambridge

4.98 out of 5 average rating, 51 reviews

Cozy Cottage on the Bay

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

A cozy cottage exterior is presented with a stone patio featuring four white Adirondack chairs surrounding a small table. A flagpole with an American flag stands nearby, while trees and greenery provide a peaceful backdrop.

Cottage in Easton

4.88 out of 5 average rating, 49 reviews

Loon Cottage on Leeds Creek

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

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