Family-friendly holiday rentals in Calvert County

Eric is an amazing host and person! Super friendly when it came to using the amenities and made us feel at home. Has great recommendations for food and local attractions. Beautiful property to walk around or just sit outside! Overall a 10/10 experience while staying at Eric’s home, couldn’t have asked for a better host for our weekend!

Fantastic house in a great location. The surrounding park is beautiful and the location is incredibly peaceful. The house was great and met our needs perfectly. Two beds and a pull out sofa. Living room and kitchen has everything you’d need. Check in and out was as simple as possible. Enjoyed staying here!

This house was absolutely central to all the activities we planned for our trip to Annapolis. Located in a wonderful neighborhood and a beautiful walk away from a tasty coffee shop!

Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

We had a wonderful stay at Brenda’s place! The pool is amazing and the whole outdoor area is great. With the grill, chairs and tables, outdoor fire (two of them!) we had such a great weekend escape. Very quiet area, we didn’t see the hosts the whole time which made it feel private. They were so responsive and helpful all weekend. Wonderful stay and we will definitely be back!

Natalie’s place was just like the pictures. Everything was clean and well stocked for our stay of 6 adults. The sunsets were beautiful from the dock and the kayaks were a definite bonus! We enjoyed time outside on the dock, deck, and in the hot tub! The beds were very comfortable and our stay was great!

The ultimate Maryland water experience. Beautiful house with perfect amenities to enjoy the bay. With the dock, the view, the crabbing, the fishing, and the kayaking, you save time and money by having everything at your fingertips. The hot tub was wonderful even in summer. The house has everything you could want for a relaxing stay. We ate the crabs we caught every night for a week! Plenty to do and see in the area, too. Definitely want to return!

We thoroughly enjoyed our stay at Laurie's home! It was a great location and the home matched the description. We had everything we could have asked for and more, and Laurie was a great host. Would definitely stay there again!

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

Stayed here Memorial Day Weekend with my family of 4 and dog and had the most lovely time! The house is very clean and conveniently located to everything! Thomas was an excellent and communicative host. We will most certainly stay here again!

David and Elizabeth’s place was perfect for my fiancé and our dog Kai. We attended a music festival at RFK and it was a short drive away. We actually ended up riding scooters back because it is so close by! There are so many restaraunts and things to do within walking distance. Check-in was super easy and it’s a very homey, comfortable space. The kitchen has a small fridge, toaster oven, microwave and hot plate with pots, pans, and everything you need to prepare a basic meal. We were able to set our dogs crate up (he’s a medium sized husky) perfectly and still had plenty of space to move around. Finding street parking was super easy and close by. You can hear noise from above at times for sure… ear plugs and a night time noise machine are provided to help. Overall we enjoyed our stay!

Exactly as pictured and described. Perfect stay and plenty of room. Beautiful back decks and yard. Great neighbors. Would stay again next time we are in the area.

This was a beautiful condo with plenty of room for everyone to spread out. It was so well stocked with everything you might need- more like staying with a thoughtful friend than at an Airbnb. The area was convenient to the metro yet really quiet for sleeping (even with kiddos who go to bed around eight). The pocket park just a block away was a perfect space for our kids to play. We would definitely stay here again!

We've stayed at Kopal's quite a few times - very peaceful neighborhood, very close to Lake Artemisia, which is lovely for walking, also very close to College Park. Great location. The house is always very clean, well-equipped and Kopal is so responsive.

Cute place in a small community of vacation homes. They don't call the area Tall Timbers for nothing. I like the corner market up the road, the restaurant and bar are old school, friendly, and lively - packed with locals.

Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

WOW. This was one of the most wonderful homes we’ve ever stayed in. Everything was clean, comfortable and accessible. Marissa was so helpful with recommendations, flexible check-in times so we could get my little one down for a nap, my three-year-old love the pool, dedicated playroom, toys, swing set and s’mores that were such a perfect gift from Marissa. My son asked if we could move there! My husband and I loved the kayaks and pond. We saw bunnies in the morning - it’s truly magical. It’s so private and just 2 mins away from town. We made so many memories and I can’t recommend staying at this property enough.

All I can say is WOW! We were blown away at the beauty of the home AND the view! Relaxing and peaceful. The pool was to die for and Kathleen was one of the best hosts I’ve ever had in all our air bnb travel!!! Will definitely return AND will check out her other properties in the future. Thank you to Kathleen and her staff/team!!

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

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

Outstanding home with so much to offer! The description is exactly what is offered. The kitchen has everything you need to prepare any meal. All bedrooms are spacious and comfortable. As far as the entertainment factor - WOW! The outside is beautiful and the pool and hot tub were fun to use. There’s so much available in this house. You will not be disappointed. Dan, the owner, was very easy to get in touch with and to work with. If you’re looking for something, ask Dan, he probably has it!

we stayed as a family of four, two adults, two children. Edwards place was gorgeous, clean, and felt bigger than in the pictures! My favourite spots were the little balcony from which you could see the water and the stars, and the STUNNING garden with beautiful pool and hot tub. The beds were so comfortable, and the pillows were perfect. There was tons of storage available in the bedrooms. The kitchen was so well appointed, and had every tool and gadget you could likely need! We walked to the Dockside tiki bar, and a short drive to all other spots. We also loved walking to the beach nearby. Edward was a great communicator, and answered any questions very quickly, and was proactive in sending information about getting into the property, using the pool etc. A true 5 star spot!

The cottage was the perfect serene retreat. The kitchen was well stocked so that we did not need to go to a restaurant for many meals. We especially enjoyed sitting on the dock to read while taking in the gorgeous view. We also brought our own kayak and took advantage of the boat house where we could store the boat overnight. Ann was a fantastic and responsive host! We will be back!