Beachfront vacation rentals in Southern Maryland

We had such a nice visit! Ryan was very responsive to questions and requests. The house is very cute and perfect for a family with kids. Lots of toys and games and outdoor equipment - and a fun tree swing! The little sandy area was just right for our three kids (ages 1, 4 and 7). We ate all our meals outside on the deck overlooking the water. The neighbors were very friendly. Everything was great!

Awesome house and location. Very nicely furnished and stocked with more items that I am accustomed to for an air bnb.

What can we say? John's property was everything we hoped it would be. The back yard is full of fun yet also serene and peaceful. The water is perfect for floating in a tube, kayaking, or just wading in and cooling off. The house has everything anyone could want. As an added bonus, you'll enjoy watching an Osprey family, Herons, Ducks, Mockingbirds, Blue Jays, Cardinals, and even some Minks and a Groundhog. The firepit is perfectly placed by the water for a morning fire as the mist rises, and especially in the evening for spectacular sunsets over the bay. Even getting there is a joy, as you go down a quiet country road lined with beautiful farms, quaint churches, and plenty of deer and wildlife. If your looking for a tourest trap vacation, then Leonardtown is not for you. But if you want a quiet getaway with all the amenities, then this is your place!

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.

We had a truly wonderful stay at this Airbnb! The house was nice, cozy, and felt like a home away from home, which made it easy to relax from the moment we arrived. The view was absolutely breathtaking—we found ourselves simply gazing out and soaking it all in. A highlight of our trip was the time we spent fishing on the beach; it was peaceful, fun, and made for some unforgettable memories. What made our stay even better was the warm and welcoming family next door. They were incredibly friendly and went out of their way to help us with the few questions we had. It was a small gesture that made a big difference. This place was everything we hoped for and more. We'd absolutely recommend it to anyone looking for a serene, comfortable spot to unwind and enjoy nature.

We loved our weekend stay at Melanie’s place!! It was clean, easy to access and a lovely location!! She was super helpful with our questions about the areas and places she recommended. Definitely recommend!!

This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back

House was larger than expected, very clean with a well-stocked kitchen, and had numerous seating/gathering areas both inside and out. Host was very responsive from booking through checkout. I would certainly stay there again.

Absolutely beautiful stay! The cabin has the cutest theme and the proximity to the water was great and a gorgeous view. Abby and family was so kind, responsive, and great hosts. Would highly recommend this getaway!

Our family had such a great time staying at MJ's place last year that we came back again this summer. As before, we all loved the view, pool, firepit, grilling on the deck, and walking down to the neighborhood beach. The house was very clean and the kitchen was well-stocked. All the beds were comfortable, and all bedrooms had well-functioning blinds/shades, which is really helpful when putting younger kids to bed. The lower level bathroom had been renovated since our last stay which was a great bonus. We are looking forward to returning next summer!

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.

Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.

Our family had beautiful weather on our vacation! Everything was as described, Mary & Shelly thought of everything. We would highly recommend.

Awesome place with my t, we had everything we needed and more. Great location to disconnect and connect with one another. Plenty of space, locals, location and great amenities.

A great place to enjoy a long weekend at the Eastern shore in Maryland.

Josh's place has an amazing setting secluded all buy itself out on a point with beautiful views. You can enjoy the bay from the upstairs kitchen and living room, josh left us check in earlier and check out later so thankful for that!!

We loved our stay! Len and Shannon are incredible hosts! Every sunset from the deck was perfect! Having the convenience store below was also nice for grabbing a snack. We wish we could have stayed longer! I would highly recommend the stay! A++++++++++++++

We recently stayed at Colin’s Airbnb in Lusby, MD, and it was an absolute gem. Nestled right by the ocean, the home was quaint, peaceful, and filled with charm. The views and the serenity of the surroundings made our getaway feel truly special. Colin was a wonderful host—quick to respond, kind, and genuinely pleasant to chat with. When we reached out for local bakery recommendations for our daughter’s birthday cake, he gladly shared a few. We ended up choosing one and couldn’t have been happier—the cake was perfect! The home itself was cozy and comfortable. The IKEA bedding added a clean, modern touch and made for a restful night’s sleep. There was just the right amount of space for the three of us to relax and enjoy our time together. Thank you, Colin, for making our stay memorable—we’d love to return someday!

Great for a group/family weekend getaway. Erin and Aryn are very hospitable hosts and provided all the essentials. Everything in the kitchen and all the light switches are clearly labeled, making it easy to navigate.

This was our fourth time staying at this amazing place, and it never disappoints! The pictures really don’t do it justice the home is even more beautiful in person. The backyard is so peaceful and well kept, perfect for relaxing while the kids play. What really makes this place special is the stunning lake view, which you can enjoy right from the living room, kitchen, and bedrooms. It’s the perfect weekend getaway for our family cozy and incredibly relaxing. We always feel right at home here and can’t wait to come back again. Highly recommend!

The Haven was truly a gem. It was so private and secluded- just what we needed to relax and reset. Ashley was so friendly and provided so many helpful accommodations that you’d typically not find elsewhere, such as complimentary coffee and a stocked s'mores station. Collectively, I think my family most enjoyed using the kayaks and paddle boards to explore the bay everyday. The kids absolutely loved hunting for wildlife around the house and pond. I’ll never forget this trip!

We had a fantastic stay at this charming cottage on a private beach! The peaceful setting and direct access to the water made for a truly relaxing getaway. We especially loved the Adirondack chairs and firepit overlooking the Chesapeake Bay—perfect for amazing views and cozy evenings. The master bedroom and living spaces offered beautiful water views that made every moment feel serene and special. The owner was incredibly accommodating with check-in and shared thoughtful, personal tips that made our stay even more enjoyable. Highly recommend this spot for anyone looking to unwind by the bay!

The views are amazing!! Water view from main bedroom, living room, dining area AND kitchen. Plenty of space for every one. The bedrooms are very roomy. Host was very responsive and flexible with check in/check out. I highly recommend!

Kassandra was very responsive and communicated well. The house is beautiful with the best view. Very nice with small children as far as being able to go back and forth from the beach. My husband also enjoyed some fishing. Everything is well stocked, and what stood out most is the shed with sand toys, beach chairs, and more that are accessible so we didn’t need to pack our own. Also the amount of beach towels and regular bath towels available were great. We will definitely be staying here again.