Family-friendly holiday 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 home was the perfect place to celebrate my daughter’s graduation! We had family travel in from several states, and everyone felt comfortable and truly enjoyed the spacious layout. It was a bit too chilly to use the pool, but I’m already looking forward to booking this home again. I’ll definitely be a repeat renter!

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

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.

Communication was great. Walking distance to some great restaurants and shopping.

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!

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.

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.

I had a wonderful stay at 7 Elms. I had to come to the area for a work event in Gainesville, and my team and I decided to stay at this AirBNB. It was so lovely. Such a cool restoration of an old farmhouse, and the property was serene and wonderful. We didn't have time to explore the area, as we were working so much and long hours. the only thing I can speak to is the grocery store - and it had everything. We saw a bunch of wild animals during morning coffee time, and that was really special. I don't think I've actually ever seen groundhogs in person, and there's a hysterical duo that run the show. The hosts were easy to communicate with.

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.

Awesome house and location. Very nicely furnished and stocked with more items that I am accustomed to for an air bnb.

Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.

Our stay was great. The house is located in a quiet friendly neighborhood. The views are amazing. The house is very comfortable and so relaxing. Loved that three bedrooms each had a bathroom. The hosts were wonderful and very responsive.

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.

Greg’s place was very clean and in a great location. Walkable to markets, restaurants, and metro. The beds were comfortable. The kitchen was well stocked. It was a great place to stay during our family vacation to DC!

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!

Teenagers point of view...easy, chill, and very comfortable. Loved the pool time (2 teenage girls) From an adults point of view... loved the privacy, pool by the room. It was very relaxing and pleasant. Exactly what we needed for the weekend. We also loved the pool. Owner was very pleasant and quick to respond. We will book again.

Thank you Kenny for the hospitality and the coffee! The place was perfect and we had no issues with our stay. We both enjoyed the area and will be back again when Kenny is available of course. Appreciate it!