Family-friendly vacation rentals in Southern Maryland

Our family and friends had a lovely time in Cynthia's home. The setting is very pretty, the dock was a great place to fish and crab from and the beach offers another great hangout spot. The added bonus is that her home is just a 10-minute walk to a cute little restaurant in a marina with great oysters and cocktails.

This was a very great find. Affordable for the part of the city we were in. Lots of energy and activity around the area, with plenty of places to eat/drink within a few block radius. Close to everything you need to be close to downtown. Easy check-in process. Beautiful, clean apartment. All in all, a wonderful spot to stay.

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!

Brooke was very responsive to all of my questions. She helped whenever needed. She contacted the place when there was a slight issue and ensured I was well cared for. I am incredibly pleased with Brooke.

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!

Very nice place to stay near Gaylord convention center. Super clean condo. All the essentials are there. Lots to do at the resort as well as nearby walking distance. Having a baby in the group we did quite a bit of laundry. A laundry room was on our floor with two washers and four dryers and free of charge. We barely passed anyone on the seventh floor. We would def stay here again.

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!

Linda and Jay seemingly were put on this earth to be incredible hosts. Their hospitality is hands down the best I’ve ever experienced and only added value to this already cozy and comfortable home. They have a ton of recommendations for the area and decades of personal experience in this region. I look forward to future opportunities for our paths to cross!

This cottage was a gorgeous place to relax with my wife for her birthday. The proximity to the bay cannot be beat - especially since she made kayaks available for our stay. I would happily re-book next time I am in the area.

Nestled in the Aurora Hills neighborhood of Arlington, you'll find a gem of a listing, far enough from the hustle and bustle of Pentagon and Crystal City but close enough to be there in mere minutes. Beyond that, this locale is close enough to the District that you can be at the Smithsonian and assorted museums in no time, and can easily access the Pier/Naval Yard with a simple transfer. As for the amenities of this location, it has everything you'd need for a short to moderate stay. The shower was incredibly hot, which I preferred. So, if you are looking for a place a bit out of the mix but close enough to be in it at a moment's notice, then please look no further than this great listing.

Melinda’s place was the perfect jumping off point for our family while we spent a week visiting relatives in Fredericksburg. It was a great size and had everything we needed for a comfortable stay. I’d highly recommend and we look forward to visiting again soon!

My friend and I loved our stay! It was a lovely little neighborhood. Alex and Shelby’s place was everything that we needed. Cute and quaint. Only the slightest of pitter patters heard from upstairs. Very clear instructions for checking in and checking out. Convenient for public transportation and provided metro cards were a great gift. Would highly recommend to anyone looking for a place to stay in the DC area!

Relaxing, well-kept property and house with a view. Plenty of good food in next town over. If you haven't been to Northern Neck, stay here and enjoy some peace and quiet.

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.

It’s always great to stay at the cottage. Beautiful surroundings, clean and comfortable place with consistently unexpected details

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.

Absolutely loved this space. The location is great and allows for exploration of the city. The space itself was clean and spacious. My favorite piece was having access to the gym within the Fairmount hotel (if im not mistaken). Lastly, host(s) are extremely responsiveness. I had questions about the property prior to booking as i was booking extremely last minute and I received a quick response.

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.

Nathan has a lovely home—it feels like stepping back in time into one of old Washington’s charming houses. Everything was spotless and well-maintained, and communication with Nathan was excellent. The location is convenient, about a 25-minute walk to Capitol Hill. While the surrounding area could be better—the streets were a bit dirty—it wasn’t a big deal and didn’t affect our overall experience. We had a wonderful time in Washington, and staying at this house was definitely part of it. Thank you, Nathan!

Greg's place is perfect for a stay in DC, close to 2 metro stops and plenty of restaurants within a few blocks walk. The space is comfortable and has all the amenities one could need. The apartment is charming with exposed brick walls and you have access to a rooftop deck. Greg sent clear and detailed instructions for parking (small additional fee), access to the apartment and he was communicative thru out our stay. We had a wonderful, if short, stay and would happily stay again in the future.

We really enjoyed our stay. The pool alone was 5stars and the cleanliness and guest house was exceptionally nice as well. My grandson claimed to have "The BEST day ever" swimming in the pool. we loved the privacy and the beautiful flowers and landscaping it was perfect. I hope to be able to come back soon.

The place was very nice, clean and quiet. The apartment is spacious and has anything you need in the kitchen. The linens are soft and the bed comfortable. The bathroom is also spacious and the shower incredible. There are good restaurants nearby, a gym in the building and the neighborhood is very interesting. Kenny is an incredible host always given us the support and attention we need. He sent us a basket of fruits as a gift.