Family-friendly vacation rentals in Annapolis

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!

Calvin's place was exactly what we needed and much more. It was described accurately, yet exceeded expectations with tiny details. For example, there was not only coffee and tea available, but creamer in the fridge, too. We had a peaceful night sleep and a nice shower. I recommend this place to anyone needing a quiet space to work and stay in the area.

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!

The Woodland retreat is an amazing getaway! My sister and I were extremely happy to spend a weekend at the pool and can't wait to visit again soon!

Great place in a cute area!

It's a much better accommodation than what you see in the photos- I don't regret staying for a long time-

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.

Beautiful Home! Very comfortable, lots to do within walking distance...well stocked kitchen with quality cookware... everything spotless...looking forward to next years 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.

Terrific, clean, comfortable apartment for a short weekend stay. Melissa couldn't have been more accommodating and communcative, and I could tell she takes great pride both in keeping the unit pristine and making her guests feel welcomed and at home.

John and Adam were excellent hosts. There were very responsive to my questions and issues. I loved the grounds and very well stocked kitchen. I would gladly stay there again.

Very cute little place. Extremely private back yard. A couple of dead bugs, but that is to be expected with the surrounding woods/forest. Overall very clean little cottage. Made my wife's birthday perfect!

Jennifer was a fantastic host, very accommodating and communicative. The location was perfect with a private door in an open, well lit ally and centrally located for our needs!

We had a fantastic stay! The place is just as described - comfortable and charming, with everything you need in a very unique setting. The beds were comfortable, the kitchens was very handy, bathroom was great. I especially enjoyed learning about the history behind the building. It was a stay that I won’t soon forget, in the best of ways!

We had a wonderful stay. It is located in a nice quiet neighborhood to get a break from the commotions that often come with larger cities. There are close by options for shopping as well as a metro train station which is very easy to navigate. Stacey was responsive and helpful when we had questions about the area. The deer in the area are no joke! I sat on the couch one morning watching a doe out the window no more a few feet away eat and lay down for a rest.

Sharif was a Super host and my husband and I enjoyed staying there. Everything was clean and neat. We have family in Laurel and we are always looking for nice places to stay. We would love stay again

The location was perfect for our needs! The space was beautifully decorated, and it had everything we could've possibly needed. The bed was very comfortable! Thank you for the wonderful stay, Autumn.

This stay was perfect for our 4 day trip to DC. Edith was very responsive, accommodating, and kind. The location was great for getting around to the various sites in DC and lots of restaurants within walking distance. The space was very clean and spacious and in great condition. Honestly the ideal, perfect stay for us.

Evan’s’ place was great. It was close enough to the UMD Campus while being close to restaurants and such. We enjoyed the deck and the space.

This was our first time using airbnb, and Craig made it an enjoyable and excellent experience. When we visit again next year, I will certainly use airbnb and rent from Craig again.