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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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

4.94 out of 5 average rating, 262 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).

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Guest favorite

Cottage in Heathsville

4.92 out of 5 average rating, 145 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!

LocationValueSleep quality

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, 127 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!

FamilyLocationQuiet

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

4.93 out of 5 average rating, 103 reviews

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!

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Top guest favorite

Cottage in Leonardtown

4.96 out of 5 average rating, 266 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.

LocationValueRiver

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, 232 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!

LocationValueWifi

Top guest favorite

Cottage in Hague

4.99 out of 5 average rating, 208 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.

ValueFamilyQuiet

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

4.97 out of 5 average rating, 131 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

FamilyLocationOutdoor spaces

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

4.99 out of 5 average rating, 105 reviews

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". ✨

ValueLocationAmenities

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

4.95 out of 5 average rating, 102 reviews

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.

FamilyLocationQuiet

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

4.91 out of 5 average rating, 251 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

ValueFamilyWalkability

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, 259 reviews

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

HOT TUB IS CURRENTLY NOT WORKING 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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