Cottage holiday rentals in Annapolis

Thank you for having us! Bryan’s Road was a perfect location to unplug, reconnect with loved ones, and enjoy nature. The house was perfectly clean, stocked with anything you’d need (and more), and the hosts were very responsive. You can tell they take pride in offering you the best stay possible.

In town for the Military Bowl and location was perfect. Loved the yard and would love to visit in the warmer months! Yarrow was excellent and had great recommendations! Highly recommend!

The host was very kind, accommodating, and had a quick response time to all messages. The house is adorable and was a great fit for 5 friends wanting to get away for a night! I would highly recommend this house and encourage you to use the outdoor space!

Great stay and host was extremely kind and helpful.

We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.

Excellent stay!! Charming cottage home, a block from the water/ park and a block from the main street. Quiet, peaceful. Irmina and Alain were quick to respond to any questions and checked on us. Top notch stocked kitchen, snacks, drinks. Clean with ample space. This was the perfect location for our trip. We will 100% be back and chose this home. Thank you again!

We had a truly magical weekend getaway at this charming water view cottage. From the moment we booked, Michael was an exceptional host—extremely responsive, pleasant to interact with, and even allowed us to check in early. He replied to our inquiries within minutes, making everything seamless. The house itself was spotlessly clean and beautifully maintained. The serene views overlooking Mill Creek were exactly what we needed for a peaceful escape from the city. Whether enjoying morning coffee with a view or simply relaxing in the cozy, tranquil atmosphere, every moment felt special. Highly recommended for anyone looking for a quiet, well-located retreat near Annapolis. We’ll definitely be back!

We had such a wonderful time staying at the Lazy Crab. The house fit our needs perfectly. For a family with a 2 & 4 year old, that isn’t easy to do. The house was clean and we appreciated the extra blankets for the cool nights. The kitchen was also well stocked for cooking at home. If you’re looking for a safe and quiet neighborhood the Lazy Crab is the place for you and your family. Danielle was also a very responsive and friendly host. She even let us leave our bags at the house after check in as our flight was later in the day. Overall, this was a great experience for our first Airbnb as a family and we hope to make this a getaway for us in the future. Thank you Danielle!

Jennifer's cottage is great! It is quiet, peaceful, and private but still right in the middle of everything - a 30 second walk to coffee shops, restaurants, bars, etc. Would also be really convenient for folks visiting the Naval Academy or St Johns. We had a great time and will almost certainly be back.

Good place to crash after going to baltimore or washington w/ a rental

We had a wonderful stay at Loon Cottage. The cottage was clean and spacious- linens and beds were comfy, and the kitchen was equipped with all essentials. The neighborhood is picturesque and quiet- we loved taking walks, and watching ducks visit in the yard. The sunroom was our favorite part of the house. Thanks for a lovely stay!

Fantastic location! It is an easy walk to all the restaurants and shops in Old town Alexandria. The perfect spot for sight seeing in DC and all the surrounding areas. The garage made parking stress free and effortless. We stayed for a week and were very comfortable, this place is a gem.

Eddie responded very quickly to every question or request I had. A lovely cottage, everything was presented as advertised...I certainly felt at home!!

Nice cozy place. Quiet neighborhood. Close to DC, airport and restaurants.

The house was a perfect location on Cape St. Claire. Well furnished and comfortable. Susan is a great host.

Very nice host and very flexible check in. Navy family, clean and cozy place near the stadium and good eats. Definitely one of my favorite AirBnB's, sure to re-book next time we are in Annapolis! Thanks for the great stay! John & Angie

We had a great stay at this property and it was perfect for our visits with friends in Grasonville. The property is well represented in the photos. Conveniently location just off the main highway and just a 2 minute walk to the water front. Thanks, Michelle

My husband and I enjoyed another wonderful stay in Overton Cottage. Absolutely everything about this home is perfect for us, including the location, which gives us many opportunities for kayaking. We can walk to the Eastern Neck Wildlife Refuge, as well. The cottage itself is amazing and we always feel that we are slaying in the home of friends who have carefully chosen each decorative item, rather than a home that is clearly designed only for rental. We will be back!

What an absolute treat to stay at the Cottage at Whitehall. We had such a lovely time, we stayed an extra day! Ty & Susie are gracious hosts and we were so excited to get a tour of the mansion and explore the grounds. The private beach at the back of the cottage is phenomenal, please take the canoe out - or even go for a swim. The sand is silky and soft, it was like a giant swimming pool nearly all to yourself. My husband enjoyed the canoe immensely (the waves scare me, so it wasn’t too much for me / but if you canoe out on the Meredith River it’s much calmer). If you fish - bring your fishing gear!! (Check local laws first, of course) Absolutely do not hesitate to book here if you have the chance, highly recommended 😍

The cottage was a perfect place for a relaxing anniversary getaway. Beautiful views, peaceful setting. House is very well maintained, clean and comfortable. Easy to launch canoe /kayaks from the dock, campfire by the water watching the moonrise over the water. Perfect, would love to return. Highly recommend.