Cottage holiday 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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Top Guest favourite
Cottage in Heathsville
4.92 out of 5 average rating, 139 reviews

Waterfront Cottage w Water Access, Sauna, Hot Tub

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, relax in our hot tub, sweat in the sauna, 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 favourite
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, 118 reviews

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!

Top Guest favourite
Cottage in Leonardtown
4.96 out of 5 average rating, 255 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 favourite
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, 223 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 favourite
Cottage in Kilmarnock
4.94 out of 5 average rating, 110 reviews

Creeks End Farmhouse

At the end of a country lane, on the banks of Henry's Creek off the Chesapeake Bay and near the village of Kilmarnock, Virginia sits Creeks End Farmhouse. This charming home built in 1903 was once a working farmhouse, but now welcomes family and friends to come relax and play. Enjoy crabbing or fishing from the dock, paddling the creek out to the bay, lazing in the adirondack chairs on the wrap around deck, or napping on the screened-in porch.

Top Guest favourite
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
4.93 out of 5 average rating, 102 reviews

Sunset Point-Waterfront home&shared pier for boat!

Perfect escape with waterfront views and pier. Calling all water and boat lovers! The house is fully outfitted with all amenities you will need. Located on the point and only a quick walk to Dockside restaurant, Colonial Beach Yacht center, town boat ramp, beach and more! Pier access for fishing, swimming or you can bring your boat! Rent a golf cart to travel around town. You will fall in love with the welcoming, fun, quiet little town!

Top Guest favourite
Cottage in Hague
4.99 out of 5 average rating, 201 reviews

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.

Top Guest favourite
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, 271 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 favourite
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
4.97 out of 5 average rating, 124 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 favourite
A charming cottage exterior showcases a combination of beige siding with blue accents. Large windows provide ample natural light, while a small porch is visible to the left. The green lawn surrounds the home, enhancing the inviting outdoor space.
Cottage in North Beach
4.87 out of 5 average rating, 192 reviews

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

A block from the Chesapeake Bay and North Beach boardwalk, this charming beach cottage is the perfect place for a weekend away by the water but still close to the activities of the DMV. Great location for groups who have booked fishing excursions on the bay or families in town for a wedding celebration. During the week, enjoy easy access to commuter busses to DC, with pickup only steps away.

Top Guest favourite
A cozy outdoor seating area is showcased with a propane fire pit surrounded by decorative stones. Two cushioned chairs and a spacious sofa are positioned nearby. A bright red umbrella stands tall, adding a splash of color against the darkening sky and tree silhouettes.
Cottage in Montross
4.99 out of 5 average rating, 208 reviews

Waterfront Escape w/ Private Dock & Fire Pit

Escape to Mallard Cottage, our 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!

Guest favourite
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, 252 reviews

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

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

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