Holiday rentals with outdoor seating in Anne Arundel County

Danielle’s place was the perfect spot for a short getaway. While it’s on the smaller side, it was comfortable and worked out great for two people and our two dogs. We didn’t spend a ton of time indoors, but we loved relaxing by the outdoor fireplace in the evenings, such a nice touch! It’s about a 20-minute drive to downtown Annapolis, offering the best of both worlds: close to the city, but a peaceful escape from the hustle and bustle.

the place is perfect. clean, peaceful, convenient. Great job, Michelle.

What a beautiful little spot of heaven at the end of the long driveway nicely tucked back with orioles, bunnies and even two kitties running around outside, inside is the so quaint and comfy and clean. The view out the windows gave peace and the fireflies at night were so cool. Stanley went above and beyond to be accommodating on our trip and his place is top notch. 10/10 would stay again

As advertised. The Keurig with a bunch of coffee cups was especially appreciated.

Can’t say enough good things about our stay! Beautiful place with everything we could possibly need. The kitchen was well stocked and our host had thought of everything! Clear instructions, great recommendations for local spots etc. And the huge backyard and deck was perfect for us and our pups. Very comfortable beds and pillows too! Finally, host communicated so well and was incredibly accommodating.

What an amazing experience! This house truly felt like a home. You wouldn't know that it was an Airbnb. It felt like we were staying at a friend's house. The owners were extremely gracious. My wife and I were there for almost two weeks with my elderly parents. I can honestly say that we thoroughly enjoyed our stay and look forward to making this an annual trip back home to MD. Thank you for allowing us to stay in your home.

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Very peaceful surroundings, you are out on a point overlooking the bay, with lots of outside space to relax in the mornings to enjoy your morning tea/coffee. I loved having the real fireplace and enjoyed an evening fire on the more chillier evenings. Felt at home and comfy.

only stayed for one night but i was very comfortable. the toiletries and snacks were an appreciated added bonus.

WOW! My family and I cannot say enough great things about Jeanne's Airbnb already planning our next trip! First off the property is an oasis in itself with a massive deck overlooking the inlets of Chesapeake Bay we woke up every morning to a beautiful blue heron eating breakfast right on the dock, having access to kayaks to explore the waterways was a huge bonus too, not to mention the gazebo with a fire pit we enjoyed roasting marshmallows and talking about the days adventures as a family. The inside of the Airbnb is extremely well thought out with every amenitie that anyone could ever ask for, from a well stocked and equiped kitchen, to the king size master bed with luxurious soft linenes, to the heated fan that greets you after a perfect water pressure shower. Seriously, this place is perfect a hidden gem for sure with easy access to so many wonderful Maryland attractions. Can't say enough great things about this experience and Airbnb can't wait to return!

Linda's place was great! Easy to find, great location, very clean! A little bit away from downtown Annapolis but easy to get to. Would stay again!

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.

We had a wonderful stay at Shawn's place. It is located in an absolutely beautiful area with a gorgeous view of the water. The place was beautifully decorated, and the bed was very comfortable. There were plenty of places to relax outside with a view of the water. We enjoyed taking the kayaks out and watching the sunset each night. Shawn was a lovely host and is a genuine person who wants you to have the best stay!

Wonderful host—I felt right at home. Had conversation prior to arrival and felt like I knew her very well before arriving. The view was spectacular I could have just sat on the patio and watched the woods and water all day. Was there for a school reunion so I had other activities that I had scheduled. This was by far, the best Air B&B experience I have had. Fantastic host, comfortable, and stunning scenery. I am going to try and revisit soon.

Really enjoyed our weekend at this location! Quiet, clean, easy to walk to a lot of great bars and restaurants, and the pool table was so fun to have access to along with the small outdoor patio area. Highly recommend!

Manon's place was a cozy and quiet place to spend a few days in Annapolis area. Bed was comfortable. Nice private deck off the kitchen. Easily walk into town. Appreciated the bottled water. Of note, if you plan to cook your own meals, the induction cooktop is a one burner.

Perfect location for exploring Annapolis attractions via walking including Naval Academy and downtown. A bonus for me, all areas were wheelchair accessible (except balcony). Very clean and well maintained! Bed was super comfy!

The cutest stay ever! We rented this for our wedding as it was just steps away from our venue. Everything was perfect!

Ayman was responsive, welcoming and informative. Everything was clean and tidy. The rooms were comfortable and quiet. I would stay there again.

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.

Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.

This was a beautiful, and comfortable apartment to stay in. David was an incredible host. This was our first time in Annapolis, which is a beautiful town with a lot to do, and plenty of great places to eat. The location of the apartment was perfect, and was in short walking distance of pretty much everything. If you are looking to stay in Annapolis, this is the spot. Really comfortable, and has an awesome deck to sit outside and enjoy a beverage on. Thanks David!

Great spot!! My fiance and I stayed two nights while attending a friend's wedding in the area. The condo was clean, comfortable, and spacious with cute nautical decor making it very homey. Lots of other nice little touches such a plenty of k-cups, some small snack packs, and beach towels/chairs/pickleball gear available for use. Seemed like Kelly had truly thought of everything! Host was proactive and check-in was easy. The parking spot is directly in front of the unit and it's just one mini set of steps to get into the unit. Would definitely recommend.

The host went above and beyond to support and welcome us. Some personal attentions and help securing extra umbrellas were much appreciated! The place was perfect for our needs, beautiful view, super practical with equipment and amenities, as well as access to the charming downtown Annapolis. It being Naval Academy Commissioning Week, we didn't have much time to interact with the host over the platform, who wanted us to check-in and out via texts and share additional info, but since everything went smoothly, we didn't really feel the need either. Commissioning Week prices are pretty high: they reflect the high demand for lodging, so it was fair. Just make sure you don't book that week if you don't have to attend a graduation :) We would gladly come again!