Cottage vacation rentals in Southern Maryland

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Top-rated cottage rentals in Southern Maryland

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Top guest favorite

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

4.96 out of 5 average rating, 409 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

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

4.97 out of 5 average rating, 201 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.

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, 117 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!

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, 198 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

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

4.99 out of 5 average rating, 228 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

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, 239 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, 100 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, 159 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.

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, 169 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

Superhost

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, 106 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

Top guest favorite

A wooden pier extends into the calm waters of Chesapeake Bay, framed by gentle waves and open sky. A grassy area borders the water, with scattered leaves adding to the natural setting. Several boats are visible moored along adjacent docks.

Cottage in North Beach

4.97 out of 5 average rating, 334 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

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

4.89 out of 5 average rating, 372 reviews

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