Beachfront holiday rentals in Dorchester County

This was great for our stay in town for the Ironman 70.3! Walkable to the race venue and a great neighborhood.

What a great place to stay and relax. Sitting with your feet in the sand , kayaking , crabbing and fishing . We will definitely boom again .

Stayed for a weekend and it was a perfect place. Very clear and easy instructions for getting in and very clean. Had everything we needed. Would highly recommend.

We had a lovely stay at Patrick’s place! It had everything we needed for a long weekend on the shore. A very comfortable home. Patrick was extremely responsive and helpful, with easy check in and check out. The kitchen was particularly lovely and well appointed! The house number is a little small so keep an eye out. And the mosquitos were fierce - don’t forget bug spray! Thanks, Patrick!

This won't be a long review...just know that Britta's cottage was AMAZING, and I regret not staying longer! I will definitely be back! I hated that it rained the weekend that we were there, but the house was cozy and had enough entertainment to stay inside and be satisfied! Britta's place was literally a home away from home!

Nanette’s place was extremely cozy and as described. It was a wonderful stay with everything you would need. She is also very responsive and helpful.

We were able to check in earlier which was great tho some of us weren’t able to get there right away… we enjoyed our stay very peaceful and were wishing we could have one more day! 😊 we were going to grill burgers but couldn’t find grill utensils so just did our best inside and still turned out great!!! Thank you for your house and allowing us to stay there!

Our stay at Leslie's Airbnb was absolutely wonderful! From the moment we booked, Leslie was incredibly responsive and helpful, making communication a breeze. It's always a relief to have a host who is so on top of things, and Leslie truly went above and beyond. The location of the home is simply unbeatable – a very short and easy walk to the beach! We loved being able to pop back and forth throughout the day without any hassle. The "cozy space" description is perfect; the home itself felt warm, inviting, and had everything we needed for a comfortable stay. We highly recommend Leslie's place for anyone looking for a relaxing and convenient beach getaway. We can't wait to come back!

The area and view are beautiful and the home's decor is welcoming. The home was very comfortable for our family group and had a VERY well-stocked kitchen. The master bed was VERY comfortable as were the rest of the beds. My husband and I slept well. We all felt at home. MJ was very responsive when I had questions and communicated about the property in clear, concise language. The host provided many outdoor recreation opportunities, which included paddleboards, kayaks, and life jackets. There was a nice sized pool but we were visiting out of season so we did not use it. The exercise room downstairs has a lot of equipment. We all enjoyed our time together. Our family is asking to come back again next year. Thanks for a great stay!

Hosts are awesome and take excellent care of their property and guests.

I'm super picky but this place was exceptional. The space was immaculate. Wonderful stay. Beautiful property. Bright, spacious apartment complete with a kitchen, dining table and even washer and dryer. The bed was super comfortable and the shower had great water pressure. Breakfast was yummy! Very kind hosts who accepted a last-minute booking. Enjoyed sitting around the fire pit watching a beautiful sunset over the Choptank River. Easy access to various small towns in the area. Great experience and would definitely stay again!

The Anchorage was perfect for racing at Ironman Maryland but would also be great for peaceful weekend getaway. Woody met us upon arrival for a tour of the property as well as providing great local dinner recommendations. The location was peaceful with great views out over the Choptank River and made for a idyllic morning breakfast setting (including Woody's world famous corn muffins!) You won't be disappointed staying here aside from the fact you will want to stay longer.

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.

Beautiful, unique and scrumptious hand-crafted breakfasts (locally sourced and in season) were spectacular! Pristine, comfortable, relaxing. Lots of activity options on site (kayaks, golf balls, painting, hammocks, croquet, bikes, swimming pool, huge private river front space). Woody and Michelle are lovely and do everything they can to make guests comfortable on site, and they recommend local spots to enjoy. Blue Ruin in Cambridge was a major highlight - we never would have found it if they hadn't suggested it. The Anchorage 1800 is the perfect place to bring friends & family and make it a group trip weekend!

Great location. Beautiful grounds by the river. Clean and comfortable rooms. Great breakfasts. Every suggestion for local attractions, dining and sightseeing locations made by the hosts were spot-on. It’s a lovely place for a relaxed, enjoyable getaway.

This house is perfect for Ironman Maryland. The pool was refreshing and the house was pristine. Ryan and Phil were wonderful host with great communication!

We had such a wonderful stay! The kitchen was incredibly well stocked—honestly better than my own at home—with 5-6 large pots, an Instant Pot, every spice you could think of,peelers (which saved me!), and both a NutriBullet and a regular blender. It made cooking for the family a breeze. The kid had a blast on the trampoline, and we all loved the easy beach access with calm waters perfect for swimming all day and kayaking. The beach was also perfect for a peaceful morning run, and at night we could see the lighthouse light on the water. The porch quickly became our favorite spot—we gathered there to watch a rainstorm and were treated to a stunning double rainbow. The sky was full of stars at night, creating such a peaceful atmosphere. The grill on the porch made cooking super convenient. We enjoyed being close to a large park where we played pickleball. The beds were large and comfortable—everyone slept really well. Michael was a fantastic host—very attentive and accommodating.

Came down for a duck hunting trip! The place was perfect! Very clean and cozy! Hope the owner was very attentive and quick to respond with any questions! If in the area again I will definitely book again!

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!

Peaceful point was stunningly beautiful! A perfect place for adults and kids to unwind and enjoy the scenic views and beautiful nature. Joanna was the best host and surprised us with a little welcome package with a kind welcome card and some of our favorite treats from Trader Joe’s! She was so helpful and responsive via text. Can’t thank her enough!

My family had a wonderful stay at this beautiful cottage. It is beautifully furnished and modern. The screened in porch was so wonderful to sit and look out on the river. Everything was so organized from check in and check out- and everything in between!

My family and I had a wonderful time! The home is private, clean, and peaceful. I recommend it to anyone seeking a private waterfront home.

We absolutely loved this place. It was a short drive to the bay and certainly worth it. The cottage was secluded enough from the neighbors and we could hear the waves with the windows open. The beach was a very short walk from the cottage and was also very private. We spent a good chunk of our time finding sharks teeth and relaxing on the porch. Grocery stores and gas stations are also fairly close. We even booked our stay for next year already.

My daughter and I stayed here for a girls weekend and it was everything we wanted and more! As soon as you walked in the door, you felt relaxed and cozy. The place was very spacious. It is way bigger than I thought it was going to be and it just gives off a cozy comfy vibe. It’s beautifully decorated and the view outback was the cherry on top. Absolutely stunning! The home had everything you needed. The kitchen was completely stocked, tons of extra linens and towels, and they left a little gift basket filled with snacks on the counter. The host was also super friendly and accommodating. We really enjoyed our weekend and hope to go back soon! Thank so much!