Family-friendly vacation rentals in Annapolis

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

Marissa’s home was beautiful and had everything we needed - plus some. Plenty of clean/comfort space and restrooms for our party of 6. We had such a relaxing, warm stay during a snowy January weekend - even smores! Marissa was always responsive and provided suggestions for shopping and dining in St. Michael’s. It was lovely all the way around! Highly recommend this home and working with these owners. Top notch!

Super experience, the host is very helpful and the location is hard to beat. It’s my second stay and will surely return. Highly recommended.

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

Cal and Colleen are very friendly, hospitable, and a goldmine of local information. The suite was well equipped and comfortable with a roomy sitting room and great outdoor space.

This place was great. Greg had clear communication and the apartment was very clean. The location is hard to beat here. The only place I went that wasn’t a quick walk and/or short metro ride away was the Nationals stadium. I had a family of five, and this was plenty of space. I would stay here again!

We were a three-generation family of 5 who had a truly great stay here. It was super clean and has character. We were happy for the coffee, ease of parking, and local places to go. Was so great to be in a lovely neighborhood that was a short drive to the National Mall. Nathan was helpful, friendly, and responsive. Kids loved the board games. Thank you so much for a fantastic DC trip!!

The Nelson Group were the perfect host/hostess during my stay at their beautiful home. They are very accommodating and responsive to the needs of their guests and went above and beyond to ensure my stay was a truly positive experience. I would definitely recommend this property with a 5 star rating! Thank you Nelson Group for your hospitality!

Absolutely Beautiful home!! Large yard. The Dog kids had a blast running after each other!! lol. Very spacious and loved the open floor plan and kitchen!! Outside fire pit what a plus!! Can’t wait to rent this again in the future!!!

This is a very well-renovated top floor 2br. It's very quiet (they installed a very solid floor) and the overall vibe is a perfect mix of modern convenience with century-old DC charm. We had one small question while we were there and the hosts responded immediately. Great stay.

It was very nice staying at Stan's cottage. It's like a tiny oasis in this rapid world of technology, and chaos. Very peaceful, quiet, cozy, and clean. CJ greeted us when we arrived, helped us with our bags, and cut fresh flowers for me when we arrived (super sweet). We got great recommendations for restaurants and take out. And finally, it was a true pleasure spending our last minutes with Stan. We enjoyed hearing about his love of travel and of birding...it would have been nice to stay a little longer...we look forward to hearing "the adventures of Stan" someday soon.

His place has everything you would need. There were lots of snacks that were left for us, as well as kitchen basics for cooking. Lots of toiletries in case you forgot something.

The apartment was lovely and it’s situated in a peaceful neighborhood with easy access to restaurants and metro. We had a great experience! We had trouble finding a parking spot one of the nights, but overall the parking worked out fine. We would recommend this place and the hosts were great!

We really enjoyed our stay. The house is lovely and in the perfect location, we walked to parks and to pick up bagels. The kitchen and bathrooms had everything we could possibly need. Everyone felt immediately at home and comfortable.

Great host. Very responsive and helpful. Home is as described and exactly what we needed for our long weekend. The many children’s items were so helpful! Makes such a big difference when traveling with little ones. The home is in the flight path of DCA and there is some noise from the airplanes that can be heard inside the house. Could be bothersome to some people at night, but for us it was easily fixed with some earplugs and a white noise machine. Street parking was busy but we never had an issue getting a spot. Thank you, Willie!

Fantastic find right in the downtown old city area. Parking was easy and the place was located in walking distance of the waterfront and shops. Beds were comfortable and the kitchen held many amenities you don't always find available. This made staying in and cooking at home very easy. Instructions were super clear and response time was immediate. We would definitely return to stay at Joel's townhouse again. Thank you!

We were two families who stayed together at Colin's place (including 3 kids). Colin's place was wonderful, and Colin was very responsive to minor issues or questions we had. The home was clean and tidy and as described in the photos. One issue we had was that the toilet door downstairs, bathroom door upstairs and some of the bedroom doors did not close properly, so it was tricky to maintain privacy. It was also very noisy outside the house due to ongoing construction, which we understand is beyond the host's control. Other than that, great location, well appointed kitchen and spacious living area and basement to spread out our things. Colin was kind enough to let us extend our check out time by a few hours, which we greatly appreciated.

This was an ideal home for our vacation in DC. The location is an easy walk to a Metro station and also quick easy access to all main roads in DC. We had a rental car and loved that it could be parked behind the house, making it quick and easy to return home. Another fun plus was the easy access to the Congressional Cemetery which ended up being a beautiful walk in the spring. The kitchen was well stocked and worked well to eat in, which we did often. DoorDash from the Roost was fast and delicious! Katie and Ryan were excellent hosts, very communicative, and genuinely went out of their way to make sure we had a wonderful stay. The house was just as pictured, the bathrooms had wonderful showers, and the beds were comfortable. We would definitely stay again if ever in DC!

Gillian and Boe were great communicators and super friendly and helpful. Everything was easy! A great stay. For detail-minded visitors: the bed was VERY comfy. And the shower is not large (stall size) but awesome water pressure and heat - felt like a mini-spa in there, a real treat :) We came during peak of spring in DC and their yard was full of beautiful blooms - a delightful bonus.

Courtney's place was perfect for our trip! The neighborhood is beautiful and quiet, there are restaurants just a short walk away, and it was a quick drive to downtown. The place was very clean and comfortable with some natural light despite being a basement apartment. This didn't bother us because we had to be up early, but if you're a light sleeper be aware that the sound travels from above since it's a basement apartment.

Our most favorite Airbnb! Beautiful, peaceful, and close to charming Chestertown. PJ is such an accommodating and gracious host. Cannot wait to come back soon. 💙

The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.

Only stayed for one night, if I'm back in the area I would stay here again

Susan’s home is incredibly warm and inviting—it truly feels like staying in a loved one’s house. The neighborhood is peaceful and safe, with friendly neighbors and a great park nearby. The house itself is charming, with comfortable beds, a cozy sunroom, and a beautiful backyard for the kiddos. The layout was functional and practical for our family of four adults and two kids. We were able to enjoy the common spaces together very comfortably while also being able to retreat into our individual spaces for privacy. Street parking was always available, and check-in/check-out were seamless. Susan was incredibly kind and responsive, making us feel right at home. It’s clear this is a cherished home, not just a rental, which adds to its warmth and character. While there’s not a ton of storage space for clothing, it wasn’t an issue for our 3-night stay. We’re already looking forward to our next visit!