Family-friendly holiday rentals in Anne Arundel County

This place is awesome!!! Very quiet and nice neighborhood. This was the place that I chose for our 11 th wedding anniversary and could not ask for a better experience. The kitchen is what I loved the most . Many places to eat near by and the Chesapeake bay is right there.

Overall a great place. It's only a short 10-15 minute walk on sidewalks to the rest of Eastport and the Annapolis harbor area, but in a quiet neighborhood that isn't busy with vehicle or foot traffic so it was easy to enjoy the lovely garden and patio outside with minimal city noise. It is accurate as described and from the photos. Did not experience any problems in the neighborhood or feel unsafe.

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!

Great place to stay with family and friends. Very quiet area and a lot of parking available. Instructions was easy to follow in and out. We recommend this place for others.

Outstanding home with so much to offer! The description is exactly what is offered. The kitchen has everything you need to prepare any meal. All bedrooms are spacious and comfortable. As far as the entertainment factor - WOW! The outside is beautiful and the pool and hot tub were fun to use. There’s so much available in this house. You will not be disappointed. Dan, the owner, was very easy to get in touch with and to work with. If you’re looking for something, ask Dan, he probably has it!

Fantastic stay. Veronica was an excellent communicator from pre-booking to check-out. House was very nice, but the pool was exceptional. Home was as described. Thanks for a great weekend.

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.

Sharon’s place was just as described. It was a convenient home base close to our family that we were visiting. We were very happy that our dogs were able to join us. There are a decent amount of steps down to the suite that we had to assist our senior pups with. The suite was clean and had a basic kitchen set up good for coffee in the morning or reheating take out. The location was very convenient to all local things to do. We were very happy with our stay.

We appreciated the opportunity to stay in this home during our son's Commissioning Week. The drive to USNA was easy and it was nice having a quiet location not too far away from Annapolis. Plenty of grocery shopping, restaurants, etc nearby. We would definitely rent this home again or recommend it to others!

Perfect location if you’re in Annapolis for a game or just to visit the city. Christopher’s house was the perfect location and distance from everything in the city. Also, very spacious and nice house perfect for me and my 4 other friends.

A friend and I stayed here for about a month during our work’s busy season and we can’t recommend the house enough. The home itself is very nice and has all the amenities you could need, whether that be in the kitchen, with the bedrooms, or with the living space itself. The house is within walking distances of a lot great restaurants and bars in Eastport, as well as Downtown Annapolis itself, so there is plenty to do. Lastly, the hosts are both responsive and friendly, so if there is anything that you need assistance with don’t hesitate to contact them. Overall, we enjoyed our stay here and are sure you will too.

Peaceful little getaway literally 10 minutes away from any restaurant or shopping you could want! Accommodations were perfect for our visit to the area to attend our daughter's promotion ceremony, only 15 minutes away from base! Beds were extremely comfortable and we were happy there was ample room for 4 adults and 2 small puppies. Would definitely stay 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.

What a gem! This cabin hidden in the woods is a perfect getaway location! The cabin itself has great heat and A/C (I got to experience both over 3+ weeks!), excellent hot water pressure in the shower, and the most comfortable bed! In addition, it's fully equipped with everything you could possibly need! Beyond the cabin, the woods are so peaceful, with deer, foxes, squirrels, and badgers! The dogs and I loved our multiple walks per day with not a person in sight. To top it off, Ted is the nicest host I've ever had! So wonderfully friendly and responsive. I hope to stay here again soon!

We had an amazing stay at this property! The space was exactly as described. Ingrid was incredibly responsive and thoughtful, providing clear instructions and great local recommendations. The location was perfect—quiet, safe, and close to everything we needed. We’d absolutely stay here again and highly recommend it to anyone looking for a hassle-free and relaxing stay.

We had an amazing time aboard the Zep Tepi! The boat is beautiful and spacious and the marina and setting are lovely! If you want to really get away and experience sleeping with the peaceful rocking of a boat, book this now! Chelsea was responsive and helpful as we got used to the workings of a boat too.

We’ve stayed here for a few years now. His place is always clean and quiet. Beautiful location and very comfortable.

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

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.

The Host the best of the best. Very attentive and very helpful when you need anything. This is the best place I have stayed. The entrance is very safe and easy. The cleanliness in the room and bathroom and the towels are very clean. The calm and peace on another level. I can say that I recommend this place as a 5 star suite and 100% sure