Cottage vacation rentals in Calvert County

Very cute place with a great view

A fantastic weekend getaway! Natalie’s home is beautifully located, offers spectacular views, and is incredibly well appointed with thoughtful touches like extra plush towels and spices and coffee. We enjoyed everything and even though the weather did not cooperate we had days of exploring the natural beauty, history, and local towns.

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

I have been doing airbnbs for over 5 years, this was the cleanest home ever, and The most comfortable beds I've ever slept in. And having a 12-year-old grandson who is very energetic, We love to play the Wii bowling and a few other of the Wii games. we got to watch some fun with us downstairs. The sauna was wonderful. these people are amazing in the house was amazing.

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!

Great stay and host was extremely kind and helpful.

This lake house was such a magical place. Being connected to nature, within the woods and by the lake, we enjoyed the serenity and quietness the entire trip. The house offers lots of space and comfort for a large group (we were 10). We took advantage of all the amenities including kayaking, watching a movie, lighting a fire outside, and the hot tub. No issues at all and hosts were super responsive and friendly!

We stayed here for two days in April, and it was great. The direct access to a bit of beach was awesome. Our kids spent hours searching for shells. The view of the bay through the trees from the house was lovely. We ate our meals on the deck, and enjoyed the hot tub. All around a great spot!

Irmina and Alain’s Little Anchor Cottage was perfect for a spring break getaway ! There was a thoughtful basket of yummy snacks and chocolates waiting for me when I arrived. The house itself has so much character yet they have put in modern amenities that make it all the more enjoyable, when staying there. Communication with Irmina was stellar!

We had a great stay at Shipwright Cottage. The queen bed & pillows were extremely comfortable, electric fireplace was very cozy for a chilly weekend and there was great water pressure in the shower. The sinks in both bathrooms are extremely tiny, but they work. The porch is not screened like the photos show, but it wasn't an issue for us due to the weather. There are water views from every room and it's a very peaceful and serene spot. We enjoyed walking along the lane in the mornings and watching the blue herons on the piers. We hope to visit again once it warms up to take advantage of the bikes and kayaks!

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 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.

Nestled in the tranquil riverside landscape of southern Maryland, just beside the southern Chesapeake Bay, this home is a hidden gem—truly extraordinary in every sense. If you're seeking a brief escape from the bustling energy of Washington D.C. or Baltimore, this haven offers the perfect retreat. We were two families with four children—two young adults heading to college and two spirited middle schoolers—and every one of us, regardless of age, found joy and peace here. From the breathtaking natural surroundings to the simple pleasure of kayaking through calm waters, each moment felt like a gentle reset for the soul. What truly elevated the experience was our host, Shawn. More than just a “super host,” she embodied hospitality in its finest form. Her attention to detail, her care for comfort, and the thoughtful touches throughout the home surpassed even the details of a Hollywood studio setting !

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.

Love the back porch with water views, very peaceful. The cottage was better in person than depicted on the photos, such a cute place! The bed linens were cozy on super cold nights. Deale is an adorable town.

We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.

Hannah’s place was perfect for a short weekend away from the DC area! The kids loved the little beach nearby as well as going to the larger parks to hunt for shark teeth. Bringing the dog along was an excellent benefit! Would recommend!

Very thankful for Danielle’s hospitality and flexibility! We were a last minute booking and had to extend more than once while waiting on movers for our home, and Danielle was ultra helpful in the process. The house was clean, cute, and in a great location for beach visitors. We will absolutely be checking to make sure either the Lazy Crab or Blue Crab are available when we plan to visit the area again! After a cross country trip that consisted of several underwhelming hotels and stays along the way, Danielle’s property was a much needed refresher for my family!

House is very cute and inviting. Couch was a little uncomfortable. Was able to host Thanksgiving for my family. My adult children stayed the whole time too. Which they enjoyed their private rooms. Close to restaurants and in a nice friendly area. Host was very responsive. I would recommend to anyone and would stay again.

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!

Nice, cozy place for two and a pup. Gorgeous views directly on the bay, especially from the bedroom. Very clean and stocked with everything one would need - nice furniture and the gas fireplace was lovely. Perfect spot for a quiet winter getaway.

Had to visit for an extended period of time for a family-related health issue. Having a place to go back to during my long stay and work was super important to me and this place delivered. What I wasn’t expecting was it’s outstanding location in the heart of North Beach (less than a block away from several restaurants and a 3 minute walk to the boardwalk), as well as it’s off-street parking which has been traditionally rare in North Beach when I’ve stayed at other airbnb’s. The house was clean, quiet, and convenient. I especially appreciated the small study where I was able to work remote during my stay. All in all, this made my stay far more pleasant than I was expecting and I definitely recommend it to anyone staying in North Beach for sure.

Lovely stay. Tom & Julie very responsive and helpful. Beautiful view across the creek with a different sunrise every morning.

We just had another wonderful stay at the Cozy Cottage in North Beach. The house is just lovely and quite comfortable. Our dog Frankie certainly felt as relaxed as we did. The view from the large front window is just great. The Chesapeake Bay, and all the dog walkers on the boardwalk are just amazing. Jerome and Carrie are always friendly, responsive and accomodating. Last, but not least, we can't wait to go back.