
Cottage vacation rentals in Southern Maryland
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Top-rated cottage rentals in Southern Maryland
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Vacation rentals for every style
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Popular amenities for Southern Maryland cottage rentals
Cottage rentals with a hot tub

Waterfront cottage w/hot tub/ gated/ pier/ firepit
He was a great host and the neighborhood was perfect for us with little kids ! We had a wonderful weekend away!

Waterfront Cottage, Pier, Sunsets, Hot Tub,Kayaks
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!

Cottage on Solitude Creek, Hot Tub, Pool & Firepit
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.

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

Cozy Cottage close to Beaches & Solomon’s Island
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!

Nautical Vibe Walk 2 Harbor Pubs USNA
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.

Bay cottage 🏖on the beach. Stunning views🏝
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.

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
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

The Little Anchor Cottage, St. Michaels, MD
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.

“Little Sligo” Historic Downtown Cottage Near I-95
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!

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
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!

Bayside Cottage- In the Town with views
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.

Charming Waterfront Home with Expansive Views
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.

THE PRINCE COTTAGE WITH PRIVATE PARKING GARAGE!!!
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!

Bell Estates I Beautiful Cottage I *Beach Passes*
Great stay! The house was clean, cozy, and had everything we needed. Daniel was a fantastic host, very friendly and responsive. Highly recommend!

Shewell’s Cottage by the Shore
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

The Colonial Cottage of Alexandria
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!

Enchanting Edge of the World Cottage
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 :)

Charming Waterfront Cottage with Sunset Views
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 !

The Little Blue Cottage
Loved the cottage! Quiet, peaceful, and homelike, just what we were looking for. We particularly enjoyed the fishing and crabbing- would definitely return!

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

Harbor Cottage
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!

Elk Cottage-Lake Lariat / Private lake access
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

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Perfect location. Spent all our time on the dock and porch when it was too sunny.
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- National Museum of African American History and Culture
- District Wharf
- Smithsonian National Museum of Natural History
- Sandy Point State Park
- Arlington National Cemetery
- Washington Monument
- Georgetown Waterfront Park
- National Air and Space Museum
- Great Falls Park
- National Harbor
- Smithsonian American Art Museum
- Lincoln Park
- Meridian Hill Park
- Congressional Country Club
- Quiet Waters Park
- Lee's Hill Golfers' Club
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Library of Congress
- Gerry Boyle Park