Holiday rentals with outdoor seating in Maryland

We visited Southern Maryland for a family wedding. The property is beautiful and peaceful. Beds are comfy, house comfy, and they thought of the little things like : a full sized ironing board & Iron, beach towels, good soaps, and all you need for s’mores!Their welcome handbook was very detailed. Our only regret was that we could not spend more time on the property itself (because of family events). Would have loved to use the kayaks and the fire pit. My brother did use hot tub. Great stay! Highly recommend

We had a short but nice stay here! We really appreciated the quick responses and thorough explanations of everything. We also appreciated the cookies and couple of waters that we so desperately needed after such a long trip! The place itself is just how it looks in pics and isn’t too far away from the downtown area ☺️

It was perfect for what we were looking for. Location was convenient to Annapolis, but in a quiet area and right on the water. It was a peaceful and restful weekend!

This was our second time staying at Kimberly’s home, and it was just as magical as we remembered. The views of the water are absolutely stunning—whether you’re enjoying your morning coffee or winding down in the evening, it’s hard to look away. The location is perfect: peaceful but just a short walk to shops and restaurants. We also really appreciated the Peloton and treadmill—such a bonus for staying active during our trip. Everything was spotless and thoughtfully prepared. Honestly, we didn’t want to leave. Already looking forward to our next visit!

Kenneth has a beautiful well located home. He was very accommodating to my needs and response was immediate. Highly recommended to those looking for rentals near the Fell's Point/Canton area!!

Right across from the St Johns lawn, walkable to all things downtown Annapolis and USNA! Cute space with all the amenities. Private entryway and off-street parking spot. Easy check-in/out instructions. A great little place to make home base for a stay in Annapolis!

This is a beautiful home in a serene setting. Although there was plenty of boat traffic it was I. The distance and not noisy at all. The home is furnished simply but there are many more amenities than most airbnbs including children’s equipment and toys! The host readily honored a special request! The pictures are not clear about the water access. It is not a beach, but a stairway. We still spent much time at the water’s edge, and sitting in those great Adirondack chairs!!

Scott and Melinda's place was perfect for a peaceful getaway for our family of 5. The water was so nice to wake up to and fall asleep hearing the water move by! The thought of all the basic needs and had everything easily accessible from fresh eggs from their chickens, a great variety of coffee pods and creamer, and all the other small needs that come up while staying in an airbnb. This was great since it is off the beaten path. If you are looking for some peaceful family time or a secluded retreat with friends, this is a perfect place!

This was a great place. It exceeded my expectations. She even had the snacks I like. I could swear it was like she read my mind. Lol. Overall, I enjoyed my stay and would come back.

Very quiet, rural setting. Perfect place to go to get some rest and do some deep work (no TV or other distractions in the apartment). Comfortable bed and linens. A few small changes were made to the unit in terms of furniture but nothing to make the pictures significantly inaccurate. I would definitely go again!

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.

Vickie and Scott were so welcoming and friendly. Respecting our privacy, yet nice conversations on our way in and out. The views, pier, and accommodations were exactly what was pictured and described. We will definitely be back. Location was only 10 minutes from downtown Leonardtown. Beautiful!

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.

We had a wonderful stay at this basement home. It was spotless, super cozy, beautifully decorated, and had everything we needed. The host was really, really nice—responsive, thoughtful, and welcoming. One thing to note: the listing does mention that it can be loud, and that’s definitely true at times. There are young kids upstairs, so you’ll hear running, playing, and general activity throughout the day. If you’re sensitive to noise, it can be a bit disruptive. Just something to keep in mind when booking. Otherwise, it’s a fantastic place and we truly enjoyed our time there!

This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

What a wonderful retreat! I can't think of a better place to stay where you're surrounded by books, art and the countryside.

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!

Tucked in the heart of Bethesda with a quiet charm that somehow still feels central to everything, this stay was a gem. Getting around was a breeze—whether by foot, metro, or last-minute snack run to the 24/7 CVS or 7-Eleven. The apartment itself? Immaculate. Fully stocked with everything we could possibly need—and then some. The internet didn’t blink, the TV was streaming-ready (a blessing for our nightly Netflix ritual), and we barely had to buy a thing beyond food. Rodrigo was the kind of host you wish all hosts were—attentive, responsive, and refreshingly clear with every detail. Winston, the building manager, was also incredibly kind and helpful. Bonus points for the cozy terrace, which turned into our favorite nighttime hangout spot. All in all, one of the most exceptional Airbnbs I’ve ever stayed in. Would come back in a heartbeat—no hesitation, no second thoughts, just pure comfort.

Large place, great jumping off point and close to town for my partner, my dog and myself. Very clean, and set up great to watch TV at night or work from home. And a fully operational kitchen so you don't have to eat out every night. Thank you again!

Love this clean calm space-the balcony was wonderful. Mark was super responsive, checked in on us and we had everything we needed-especially in the kitchen. Great location for walking to restaurants and stores. Will definitely stay again!

Amazing views! We watched the sunrise over the ocean from bed. The bathrooms are small with not much room to store your toiletries, but otherwise the space was great for my partner & I. We had a wonderful stay!

Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!

Shiri was very friendly and she reached out to make sure we had her number. We travelled with a one year old and she fell asleep before we could check in and they were very accommodating. They had everything, a playpen and even had beach toys as we forgot hers. The place is beautiful and in the perfect location with great instructions from Shiri. You have the perfect view for sunrise and sunset, the sound of the waves is very relaxing. The beach is literally at your finger tips. We will definitely be coming back again.

The unit was very inviting and homie. It was as describe in the listing. Brooke is a great host.I love Everything was in walking distance very convenient . I would highly recommend this spot