Kid-friendly holiday rentals in Annapolis

The house is easy to find and has a great outdoor seating area. The house and linens were very clean and Sekai even provided fresh fruit upon arrival! The stocked Kurig pods were very handy and appreciated in the morning as well. From this location you have easy access to downtown Annapolis and all of its history. If you go the other way out of the neighborhood, you can browse the mall and TownCentre for all your other shopping needs. This is a pet friendly house that you would not know there had ever been a dog in there. Fortunately, ours was well behaved so you still won't know a pet was ever there! He enjoyed walking the large private yard.

Very quiet location but not far from amenities. The home had an attention to detail that not all air bnbs do (for example enough towel hooks for everyone staying!) as well as basic cooking amenities

plenty of towels. Great accomodations for a family wedding. Cards and games were available and appreciated.

We had a great stay for CW25! The location is ideal for easy access to USNA and all that downtown has to offer. The home was exceptionally well appointed and spotless . The decor is beautiful Beds /linens were all very comfortable ( with a huge variety of pillow options which was so appreciated !)and the blackout shades in the bedrooms made for a great nights sleep.Kate is a wonderful and responsive host. We highly recommend this beautiful home!

Above & beyond! The home was in a great spot with an excellent price. Tim was extremely accommodating with our requests and communication was perfect. The refrigerator was stocked with eggs and butter. The cupboards were stocked with staples and all the supplies we needed - toilet soap, shampoo, Kleenex, paper towels, bath towels, snacks, granola bars, etc. We would highly recommend this Airbnb to anyone and would use again. Thank you!

This home is right in downtown Annapolis. You can walk to many historic sites, restaurants, and bars. There is no parking, so you must park in one of the garages and walk to the house - but it isn't far. Street parking is limited to 2 hours for non-permit holders. This was one of my favorite airbnbs in Annapolis (and I've stayed in many). It was exactly as pictured/described. It was bigger than expected with lots of space for a larger group. The living room was nice with lots of seating and a large tv. We used the pullout sofa in the second living area and it was super comfortable. The bedrooms and bathrooms were very nice - great showers and deep soaker tub in the en suite. I slept in the king bed in the back bedroom and it was wonderful. The kitchen and dining area were very nice and we gathered there much of the time. We enjoyed the front porch for morning coffee and evening drinks. The back patio was also another nice space to sit and relax.

Cannot say enough great things! Incredibly understanding, great communication and loved the space! 100% recommend!

Beautiful place, beautiful location. Joel thought of anything you could want.

This is a great place to stay and tour the DC Metro area - provided you have a car. Most days it would take us 30 minutes to get to and from DC though if we hit rush-hour, it was as long as an hour. The space is tidy and great. My kids love the pool, though it was a little cold for me-they swam there every night. Jennifer is great to communicate if you have any needs she gets stuff done right away. Note that there is only one bathroom, which can be a pain if you have a full house of six people. The washer and dryer are small so it will take you longer if you’re used to a full size. She had all the cooking methods and appliances available. The theater room has Netflix and Amazon prime ready for you to watch a show. There is even a popcorn maker. We did not use the gym, but it was nice - comparable to a small hotel gym. Property is in the owner’s basement, so there is some sound from upstairs as identified in the listing. Host stays out of your way but is there if you need anything.

Penny is an incredible host who really goes above and beyond! I greatly enjoyed my stay.

Very responsive host. The side yard is very nice for people with dogs that travel. Location is very nice but DC traffic during rush hour can be rough but this can be planned for. Would stay again.

Had a great time! Kathy and wayne was very helpful on suggesting restaurants and things to do. We loved the dock and fishing! They made sure we was right at home when we interacted with. This was a good central place to all we wanted to see, we went to Hersey Pa. Washington dc., The beach(bay) area, Baltimore harbor.

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.

Anne’s place was great for my week long stay in Baltimore. It was about 17 minutes from JHU, less than 15 minutes from the Harbor and National Aquarium, close to Baltimore local favorites, and directly across from a park. Anne was responsive to all my concerns and needs. The apartment was clean and had an abundance of extra towels and sheets for our use. The only comment I have is about the TV and Wifi which were both slow and lagged when doing work. Everything else was perfect and I would definitely stay there again.

Great place to stay in Eastport. A couple doors down from Vin 909 Winecafe, which we highly recommend.

Joyce is a one in a million host, but more importantly, a one in a trillion person... I'm beyond grateful to have had the opportunity to meet her and Nicole. Thank you Joyce for welcoming me with open arms and making my stay in Annapolis an unforgettable experience. Already looking forward to when our paths cross again. Sending you and your family blessings <3

Our stay at Occaquan was peaceful, relaxing, and very much needed. Arriving to the parking lot was a breeze, only because if John's specific instructions to find it, that was very much appreciated after a long drive. Walking into the place, first impression, looks just like the picture. The very next thought, "how cute is this". From the beautiful window behind the couch with a lovely tree to watch birds in to the cozy feeling of being in a familiar place. This place is quiet, surrounded with beautiful historic scenery, and has many local shops and vendors to spend an afternoon exploring. We walked down to the park by the water way and learned some history while soaking up the sun and the breeze of nature. I absolutely recommend John's place for a stay. I know I will be returning for a simple, relaxing get away, once again! Thank you John for everything!

Ellen’s condo was absolutely perfect for Commissioning Week. The location couldn’t have been better—within walking distance to fantastic restaurants, the Naval Academy, and Graduation at the Navy-Marine Corps Memorial Stadium. The coffee shop downstairs was a delightful bonus, and the underground parking was a major perk. Ellen provided clear and detailed instructions about the condo and guest expectations, making everything easy to understand and stress-free. The condo itself is beautifully and tastefully furnished, with all the essentials thoughtfully provided. The in-unit washer and dryer were a huge convenience. The bathroom was spacious and well-appointed, complete with shampoo, conditioner, and body wash. What I appreciated most was how quiet and peaceful the condo was—it offered a true retreat. The private patio was perfect for enjoying a morning coffee or an afternoon cocktail. I would absolutely stay here again.

We can’t say enough good things about Megan’s place. Our favorite part was how well-appointed the kitchen is, but it’s all great. Very walkable/bikeable city, so you can leave your car behind.

Quiet location. Nicely decorated. Abaad was very responsive. I enjoyed my stay.

Jordan and his place were both amazing. As avid gamers ourselves, this was a walk down memory lane. All linens and kitchen ware were available. You can cast your apps on the Google TVs, which is a huge bonus. There are tons of food places within 5 minutes walking distance and we were able to to walk to the CFG Bank Arena for a show with in 15-20 min. Saves on parking or Uber/Lyft costs. Jordan is extremely responsive and even recommended local eats. They were delicious. Thanm you so much, Jordan. It was a delight having you as a host.

Oxford is my favorite place to visit on the Eastern shore and I love staying in this little place near the town park. it's so peaceful and close to everything. I love connecting with the locals I've met on my travels. I look forward to returning!

Ben’s place is exactly as described me and my family enjoyed our stay. I felt right at home, when I’m visiting my sister in the near future I will definitely stay again.

Great location, close to transportation and dining options. Place is very quaint. Uncomplicated entry and exit. Neighborhood walkable and friendly. I would consider staying again.