Cottage vacation rentals in Southern Maryland

Find and book unique cottages on Airbnb

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Popular amenities for Southern Maryland cottage rentals

Cottage rentals with a hot tub

Superhost
An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.
Cottage in Annapolis
4.85 out of 5 average rating, 87 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

AliRating, 5 stars3 days ago
He was a great host and the neighborhood was perfect for us with little kids ! We had a wonderful weekend away!
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, 65 reviews

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks

KathyRating, 5 stars2 days ago
The house is wonderful! We enjoyed being in the fenced backyard with our dogs, hanging out on the dock watching the boats go by, or just sitting in the house admiring the view through the huge picture windows. It was very clean and had all that we needed for a relaxing get away weekend. Natalie was very responsive and very helpful with great local suggestions. Emily's Produce is only a few minutes away and has everything we needed, including fully cooked meals. We can't wait to come back!
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, 106 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

MeganRating, 5 stars6 days ago
This is our second time visiting and a perfect spot with everything we needed. Could provide more dish towels, paper towels, and trash bags but supplies were provided quickly upon request.
Superhost
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, 210 reviews

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

LorenRating, 5 stars2 weeks ago
We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.
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, 15 reviews

Cozy Cottage close to Beaches & Solomon’s Island

LindaRating, 5 stars1 month ago
Emilio and Wanda’s home was absolutely lovely. They thought of everything to make our stay so enjoyable. Would recommend to anyone wanting a relaxing stay. So very close to Solomon’s Island. Thank you Emilio and Wanda!
Guest favorite
A screened porch features a hanging bench swing with cushions in shades of blue and nautical motifs. A small chair stands nearby, adorned with a decorative pillow. Tall curtains frame the space, providing a relaxed and inviting atmosphere surrounded by greenery.
Cottage in Annapolis
4.86 out of 5 average rating, 107 reviews

Nautical Vibe Walk 2 Harbor Pubs USNA

JohnRating, 5 stars1 month ago
Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.
Guest favorite
A hot tub is positioned on a wooden deck, overlooking the shimmering waters of the Chesapeake Bay. Surrounding greenery includes tall grasses and trees, with the expansive view of the water framed by a clear blue sky.
Cottage in Reedville
4.9 out of 5 average rating, 207 reviews

Bay cottage 🏖on the beach. Stunning views🏝

JenniferRating, 5 stars3 days ago
We had a relaxing weekend stay at Dave and Melissa’s place. The views from the screened in porch were beautiful. The surrounding area had a mix of older and newer properties. The little beach was nice. Overall a great place if you are looking for a quiet place to escape to.
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
4.52 out of 5 average rating, 21 reviews

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

EstherRating, 5 stars1 month ago
I book this place for my bday I just wanted to have fun & have a break from routine but at the same time feel comfortable like home, and that’s how it was and better we all had a great time. Really nice property, fabulous decoration, great surroundings to visit, and nice backyard to relax and enjoy. The jacuzzi and fire pit unforgettable part of the trip, really nice atmosphere. If there was an issue super easy and efficient way to respond to the situation. Made my bday really special for me and my family <3

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, 237 reviews

The Little Anchor Cottage, St. Michaels, MD

RoxanaRating, 5 stars1 week ago
Great home in a beautiful area. Spacious rooms and the whole house is equipped with everything you need. I love Airbnbs that feel homey and not ‘commercial’. The area is BEAUTIFUL and walkable with great restaurants near by (checkout limonchello and get the pizza!). Perfect for a weekend.
Guest favorite
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
4.94 out of 5 average rating, 115 reviews

“Little Sligo” Historic Downtown Cottage Near I-95

KariRating, 5 stars2 weeks ago
Loved our stay in this beautiful cottage. Very clean and had all the amenities. There was a park next door that I could walk my dogs to. Also close to downtown restaurants!
Guest favorite
Cottage in Deale
4.82 out of 5 average rating, 182 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

LaurieRating, 5 stars1 week ago
The cottage was in a perfect location for my sisters and I to stay for our "sisters weekend" escape. The setting is beautiful and so relaxing. There was plenty of room for us and everything was clean and tidy. We took advantage of the kayaks during the day and had a wonderful fire with s'mores in the evening looking out over the water. We will be back!
Superhost
The exterior of the cottage features a welcoming yellow facade, complemented by a manicured lawn with shrubs and mulch. A wooden deck with white columns provides entry to the front door, which is flanked by large windows. An American flag hangs proudly to the left.
Cottage in Colonial Beach
4.94 out of 5 average rating, 170 reviews

Bayside Cottage- In the Town with views

KimberlyRating, 5 stars1 month ago
We thoroughly enjoyed our stay at this AIRBNB. It was walking distance to a nice Mexican Restaurant as well as to a brewery. We spent hours on the front porch in the nice rocking chairs. The back of the property overlooked the water which was beautiful! It was close to everything in town! The house was clean and had all of the necessities. We also enjoyed the front sitting area during the morning. The owner was responsive and helpful! We would definitely recommend this property.
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
4.9 out of 5 average rating, 103 reviews

Charming Waterfront Home with Expansive Views

JessicaRating, 5 stars2 days ago
This is my second time staying at this cottage. The location is beautiful, the private beach is great for kids, and all the welcome gifts and fresh flowers are a friendly touch. The kitchen has everything you need for cooking, and the two bedrooms made for a comfortable stay for my family of four. We enjoyed the Fisherman’s Museum in Reedsville and the local coffee, Fawn’s. Northern Neck is a lovely area and everyone we ran into the whole weekend was incredibly friendly.
Superhost
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
4.8 out of 5 average rating, 183 reviews

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!

MicheleRating, 5 stars3 weeks ago
Absolutely wonderful stay! Josh and Judy were excellent hosts—friendly, responsive, and made everything so easy from check-in to check-out. The cottage itself was the perfect amount of space for our visit and had everything we needed for a comfortable stay in the DC area. The location couldn’t be better! The neighborhood is incredibly safe, and we loved being able to walk to so many phenomenal restaurants nearby. Having access to the garage was a huge bonus and made our trip so much more convenient and enjoyable. We love Alexandria and can’t wait to stay at Josh and Judy’s cottage again during our next visit. Highly recommend!
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, 156 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

MichaellRating, 5 stars2 weeks ago
Great stay! The house was clean, cozy, and had everything we needed. Daniel was a fantastic host, very friendly and responsive. Highly recommend!
Superhost
A quaint yellow cottage is framed by a wooden fence and natural greenery. The front porch features colorful doors and multiple windows, allowing ample light to enter. A deck extends from the house, providing a welcoming space for relaxation amidst the surrounding trees.
Cottage in Port Republic
4.8 out of 5 average rating, 186 reviews

Shewell’s Cottage by the Shore

ChristopherRating, 5 stars1 week ago
We had a great stay, it was exactly the relaxing family vacation we were looking for! Hyrum and Lisa were excellent hosts and made sure we had all the information we needed and everything was going well throughout the stay. Thank you Hyrum and Lisa!

Private cottage rentals

Guest favorite
A vibrant trolley is seen traveling down a tree-lined street, with the destination 'TO KING ST' displayed prominently. Historic buildings stand on either side, adorned with flags and window details. Cars are parked along the street, contributing to a lively urban atmosphere.
Cottage in Alexandria
5 out of 5 average rating, 5 reviews

The Colonial Cottage of Alexandria

AbbosaliRating, 5 stars1 week ago
We had such a lovely stay at this cute cottage! It was cozy, clean, and had such a peaceful vibe. We especially enjoyed relaxing on the patio—it was the perfect spot to unwind. The location couldn’t have been better: a quiet, safe neighborhood in Alexandria, super close to Washington D.C., and we had no issues with parking at all! Heather was a wonderful host—very kind and quick to respond to any questions we had. We will stay here again in the future!
Guest favorite
Cottage in Lottsburg
4.98 out of 5 average rating, 87 reviews

Enchanting Edge of the World Cottage

JuliaRating, 5 stars1 month ago
Perfect Lake Side Vacation Spot!!! My friends and I spent the weekend and we absolutely loved it! The home is beautiful and the surroundings are so serine. Perfect place to get away and spend pleasurably days participating in outdoor activities like fishing, grilling and watching the sunset. We loved our stay so much we are already planning our next trip to the wonderful spot! Tim is an amazing host! Check in and check out were a breeze, he kindly checked in on us and was always prepared to help facilitate an enjoyable stay. I couldn’t recommend this listing any higher :)
Top guest favorite
Cottage in Tall Timbers
5 out of 5 average rating, 46 reviews

Charming Waterfront Cottage with Sunset Views

LeslieRating, 5 stars3 weeks ago
We had an amazing holiday weekend at Dave and Jenny’s cottage! They were always so quick to respond with any requests we had! The cottage as perfect and just like the pictures. They literally had thought of everything! The sunsets were absolutely stunning and it was truly the most relaxing time we’d had in a while! It was just what we needed !
Top guest favorite
An illustrated children's book titled 'The Little Blue Cottage' is positioned on a rustic wooden table. The cover features a scenic coastal scene, with a small blue cottage, sailboats, and various elements of nature, capturing a whimsical charm ideal for families.
Cottage in Hollywood
5 out of 5 average rating, 39 reviews

The Little Blue Cottage

AnneRating, 5 stars4 days ago
Loved the cottage! Quiet, peaceful, and homelike, just what we were looking for. We particularly enjoyed the fishing and crabbing- would definitely return!
Top guest favorite
A cheerful yellow cottage stands with a covered front porch featuring white railings and two pink rocking chairs. Lush greenery surrounds the home, with a white picket fence offering a welcoming touch. A decorative trellis adds charm to the entryway.
Cottage in Colonial Beach
5 out of 5 average rating, 35 reviews

Boaty McBeach House: Walk to Beach, Bay & Bites!

AmyRating, 5 stars3 weeks ago
Colonial Beach was the perfect destination for a girls kid-free weekend away and Matthew’s cottage was super cute and the ideal place to stay! Matthew was very knowledgeable of the town and had excellent recommendations on just about everything. The house was clean, comfortable and well stocked with essentials. The house is in a great location and we were able to walk just a short distance to the beach and many restaurants. Dockside Tiki Bar on a Saturday night was the highlight of the trip, very fun live band and beautiful view of the sunset! El Toro Mexican restaurant is hidden in a strip mall but definitely worth a try for delicious Mexican food and margaritas! Would 100% stay at Matthew’s place for another visit to CB!
Guest favorite
A close-up of freshly cooked crabs showcases their reddish-orange shells. The crabs are arranged closely together, displaying their distinctive claws and legs. The texture of the shells is visible, highlighting the natural details of the seafood.
Cottage in Montross
4.97 out of 5 average rating, 39 reviews

Harbor Cottage

JennaRating, 5 stars4 days ago
We loved our stay here! It had everything we needed for the beach and some toys for our toddler. The house is well kept and it even has a small wired fenced yard that was perfect for our two dogs. The beach was smaller than I realized but super relaxing and ended up being a good size for us. Pool access was also appreciated. Would definitely consider coming back!
Guest favorite
A lighthouse stands adjacent to a white house, both framed against the backdrop of a tranquil bay at sunset. The scene captures the shoreline, where gentle waves lap against sandy beaches, while the sky displays a gradient of warm colors reflecting the day’s end.
Cottage in Lusby
4.91 out of 5 average rating, 34 reviews

Elk Cottage-Lake Lariat / Private lake access

MillenRating, 5 stars3 weeks ago
A fantastic place to spend the weekend with your friends or family. Peaceful, beautiful scenery, and incredible vibes. Britta was also super helpful and responsive
Top guest favorite
A vibrant green kayak rests on a sandy beach, partially in shallow water. The calm river reflects the clear blue sky, with a wooden dock visible in the background. Sunlight illuminates the scene, creating a serene and inviting setting for water activities.
Cottage in Leonardtown
4.96 out of 5 average rating, 94 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

ElizabethRating, 5 stars1 week ago
Perfect location. Spent all our time on the dock and porch when it was too sunny.

Destinations to explore