Holiday rentals with a pool in Calvert County

We had such a lovely stay! The house was absolutely beautiful and so peaceful — tucked away in the country, it offered the quiet escape we were looking for. We especially enjoyed visiting Flag Ponds nearby — such a great local gem! Deborah was an amazing host. Her communication was prompt and helpful from start to finish, and she made the home feel incredibly welcoming and clean. You can tell she truly cares about her guests’ experience. We highly recommend staying here! The only thing to note was the spiders and bats outside at night — definitely a bit of a surprise for us city folks! But overall, it was a wonderful trip and we’re really grateful for such a thoughtful and relaxing stay. It made for a great family trip and get away.

We stayed at Dana’s over the weekend for a family get together in town. The home was extremely welcoming and clean! Instructions to get into the home were straight forward and easy. As our first time staying in an Airbnb, our expectations were exceeded! Highly recommend staying here! Thanks again!!

Our stay from start to finish was amazing! Courtney and Christian have a beautiful home that is in a great location. They thought of everything to make our stay memorable. The pantry was open to us, towels were folded beautifully, super clean, and they even had three Christmas trees up. We will definitely be visiting again.

fantastic spot on the Island. incredible sunsets. very clean with stunning views of the Bay. everything you need to enjoy the Island is here with walking distance general store.

Courtney was extremely responsive and made sure my stay was perfect. The property was amazing and the views were stunning. I would come back once a month if I had the time! Great property and great owner!

This farm house was beautiful and full of character. Didi was very responsive and helpful when we needed it. The instructions for operating the pool were spot on, and the pool was by far the favorite thing about this house for our kids and us. The house was well stocked with everything we needed and more. We were pleasantly surprised that there was a piano in the main living area. My kids were playing consistently. There were so many games, DVD's to watch and a full screen projector that we could stream movies too. Sitting on the porch watching the Osprey nest was another favorite. There were 11 of us and there was plenty of sleeping spaces and bathrooms for all of us. We were there during an extreme heat wave and the house stayed cool and comfortable with the air conditioners. We loved the kayaks and did take them out but since it was jellyfish season we couldn't swim in the river water. We explored the local recommendations that Didi sent to us. We had a wonderful time.

The photos are mirror images of the condo. The kitchen and bath are amply supplied with all the items needed, even to prepare meals if you choose. Accessibility features are a bonus when traveling with an individual with mobility issues. Locally, Portside Seafood was a welcome surprise with a delicious menu. It was the perfect place for my sister and me to have some downtime and recharge. Thank you for sharing your beautiful home.

Brandon’s home was as beautiful as the pictures. We loved how easy it was to walk to everything in the town. The pool and rooftop patio were an added bonus. We enjoyed cooking in the large kitchen, and the house easily accommodated our group of 8. We will be back!

We had an amazing girls weekend in large part because of how beautifully the rental was decorated, the amenities that came with it and its amazing location! We all agreed we will be looking at renting this location again next year!

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.

This was an awesome stay! If you have infants their place is a must as it is easily baby proofed and has so many accessible items!

We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

My wife and I had a fantastic stay at this charming studio in Annapolis. It was cozy, spotless, and had everything we needed for a relaxing weekend escape. The space is thoughtfully decorated with a modern touch and had plenty of natural light. The bed was super comfortable, and we appreciated the little extras like coffee, an air purifier, and fast Wi-Fi. The location couldn't have been better—walking distance to downtown, restaurants, and the waterfront, but tucked away enough to feel quiet and private. Parking was easy, and check-in was seamless thanks to clear communication from our host. We highly recommend this place to any couple looking for a romantic, convenient, and well-kept spot to explore Annapolis. We’d absolutely stay again!

I definitely loved this home soooo spotless felt right at home. You might hear people walking here and there BUT it’s not an all the time thing, other than that it’s so peaceful. Kitchen is beautiful and has all the spices you kinda need if you wanna cook, bed was sooooooo comfortable and the living room was so inviting. It’s close to food spots banks grocery stores, etc. I’m definitely booking again.