Holiday rentals with outdoor seating in Calvert County

Perfect spot in Solomon's and our group could walk to everything. Great house and would definitely stay here again!

We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!

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!

Dale is an incredibly proactive and helpful host. He checked in with us several times to ensure we had everything we need and went out of his way to meet us on our schedule to check in and show us around. This is a great spot to relax and look at the ocean or an easy commute to Solomon's Island and all its amenities. You also get access to the community's private beach, which is beautiful and a real asset!

We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

This was a cute little home to stay at over the weekend. Only downside was having to pay for beach access. But the house itself was very nice and had all the kitchen items we needed. Would stay again.

Our third year of staying at Jennifer’s cottage and studio. A lovely location for a beach weekend with our family and grandchildren. The accommodation is comfortable and well equipped, the cottage having a full kitchen and large sunny deck with BBQ. The studio is cozy and perfect for a couple. The community beach is a 2 minute walk, quiet and safe for young swimmers. We didn’t get to enjoy the hot tub or use the kayaks ( too busy with little kids!) but maybe next year!

Lori was super accommodating with our last minute booking and really friendly as we messaged back and forth. It made a bad situation at my house (dead electrical panel) an accidental 5 day vacation at Lori’s, so I really appreciated her for it! All the basics were provided in the kitchen and baths, and chargers in every room. There were even two desks, which was perfect since two of us telework. My dog is cranky and set in his ways, so he didn’t like the doggy door but I can see how it would be super convenient for a normal dog ;) And I had forgotten how much I like North Beach! Lori’s place is an easy 15 minute walk to the beach and boardwalk. Having the beach pass and beach towels provided was great, but I ended up on a shady bench along the boardwalk.

I loved the area, calm neighborhood, the inside is big enough to host up to 9 people. She respond very quick, I have good time, I would recommend it to friends.

What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!

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 rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.

Our second time here! An absolutely adorable gem of an Airbnb with the nicest hosts and most beautiful garden and dock on the River! Great restaurant recommendations, super comfortable beds, and lovely living room. Perfect for families visiting the beloved St. Mary’s River.

I came back just a few days later because I could not stop thinking about this place. The gas fireplace once again created the perfect cozy environment after long workdays. The unit is not only beautiful but also perfectly equipped for an extended stay. Everything I needed to feel settled and focused was already there. The hosts were just as wonderful the second time. Still one of my favorite stays in DC.

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!

Lynn's home was wonderful and quaint. The bed was comfortable, the kitchen and living area were perfect, and my stay was enjoyable. I'll stay again when I visit the Annapolis/DC area in the future! Thank you Lynn!

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 had a wonderful stay at Lauren’s place and would highly recommend to anyone traveling to DC!

Brandon’s home was as beautiful as the pictures. We loved how easy it was to walk to everything in the town. The pool and rooftop patio were an added bonus. We enjoyed cooking in the large kitchen, and the house easily accommodated our group of 8. We will be back!

Chris was a great host making check in and out so easy and flexible! The location of the place was perfect for walking to the market and to get coffee! The space was exactly like the pictures and perfect for a quick getaway with my fiance! Recommend this place!

Joe’s place was exactly as advertised and we loved staying there during our trip. Joe was also very responsive and helpful.

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.

My friends and I had an amazing stay at George’s place. The location was perfect, we weren’t far at all from the attractions we wanted to see. The unit was very spacious, beautifully decorated, and very clean. My favorite area was the patio and my friends enjoyed the shower with the jets after a long day of traveling. I would definitely stay again and recommend highly to anyone visiting DC.

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!