Holiday rentals with lake access in Southern Maryland

This is our 2nd time being here and we were not disappointed! This house has a beautiful view. Pooja is a wonderful host. We were welcome with a basket of snacks. Kitchen and bathroom are fully stocked. Pooja provided more than enough for our stay and we had everything we need. House is clean and beds are comfortable. My family had a great time fishing and kayaking. Thanks Pooja for your hospitality!

Creek Retreat is a perfect place to kick back and relax. Surrounded by nature, a private oasis. The space is well appointed, clean and comfortable. Tastefully decorated. Added amenities and attention to details elevate the experience. Enjoy kayaking and sitting by the fire. Georgia is a great hostess and is proactive and responsive. If you're looking for a getaway, book it here!

We had an extraordinary family time in Jen's house. Cobb island is an unexpected gem. Being on the Neal Sound of the Island was best for birding and kayaking. A magical week everybody will remember! Thank you to Jen for providing such a great place!

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.

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!

I can't express enough how wonderful this home is. We loved it so much that we extended our stay by an extra day! The location was absolutely perfect and met all our family's needs. The private dock quickly became a family favorite, along with the hot tub. It's a quiet, peaceful retreat and the ideal place to recharge with your loved ones. We will definitely be back!

We had a wonderful stay at Presley Creek! The house was clean and comfortable. The porch and with the ceiling fans was delightful! The kitchen had everything you’d need for preparing meals. The location was so peaceful. The property was huge and felt so private & secluded with woods and the water. We enjoyed the wildlife; geese, eagles, herons, otters. We brought our dogs, and they loved running and swimming! We brought all our food with us since we knew stores were not close. Also, if you want a beach, we found a little beach not too far called Vir-Mar, which has a very small public beach. Hughlett Point which is a bit farther is larger but very limited parking. If you are looking for a laid back vibe, I highly recommend this property!

Cute place in a small community of vacation homes. They don't call the area Tall Timbers for nothing. I like the corner market up the road, the restaurant and bar are old school, friendly, and lively - packed with locals.

My wife and I enjoyed our long weekend at your apartment very much. It was my wife's college reunion weekend, and this apartment was a great place in which to access everything. Great historic building that has been renovated in a very responsible manner.

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!

We had an amazing stay at Theo’s place! Everything was perfect clean, comfortable, and exactly as described. The thoughtful touches and great communication made our trip so enjoyable. We’d absolutely love to return! Highly recommend!

I cannot say enough about Paul! Proactive, great recommendations and an all-around fantastic fellow! My children, two dogs, and I had a wonderful time and would come back in a heartbeat! The place itself is immaculate and has a gorgeous view of the Chesapeake Bay. Minutes from the Naval Academy and an easy ride to the Greenbelt metro so we could catch a DC United game in the city.

Lisa’s place was amazing! My daughter and I had a great visit. The location is perfect for going into Annapolis. We will definitely be back. Thank you for a great few days!

Location is quiet and tucked away. Clean and has everything you need. Close to The highway for easy access to eastern shore towns.

We had a great stay at Kathleen's listing. The apartment is in a great location, only 15 minute drive max to all of the nearby attractions. We enjoyed having some tranquility being away from downtown after a long day and the free parking! Kathleen stocked the place with all necessities and more - including snacks and recommendations. The neighborhood is beautiful to walk around, with views of the water everywhere! Definitely would recommend staying here!

Cute and cozy! I felt right at home. Jordan and Danny are very nice folks, the apartment is very well appointed. There is a dock on the property that I should have spent more time on. The bed was a dream to sleep in and I literally overslept my alarm the first day. You will definitely need a car to get around but the apartment is a 3min drive to Safeway, Walgreens, Starbucks, etc. The neighborhood has a homey feel and the apartment has a homey feel which was my jam. My dog had a little accident but I got some carpet cleaner and let Jordan know and she was very understanding. I would definitely stay here again if I am visiting Kent Island.

As always, just an awesome getaway! The minute I pull up to the cottage and look out at the water, any stress just disappears. I’ve been coming here for a number of years and Angela and her cottage are second to none!! Angela is a wonderful host and provides great directions and recommendations and the cottage is just perfect. Thank you Angela for having this little gem!!!

The cottage was in a perfect location for my sisters and I to stay for our "sisters weekend" escape. The setting is beautiful and so relaxing. There was plenty of room for us and everything was clean and tidy. We took advantage of the kayaks during the day and had a wonderful fire with s'mores in the evening looking out over the water. We will be back!

Beautiful waterfront setting. Two kitchens (one in each cottage). This property lacks privacy on one side, with an open view into the neighboring yard. While there's no fence or natural barrier separating the two spaces, the neighbors appeared friendly and unconcerned about the presence of visitors. Would recommend or stay again.

Janet has a unique property considering the destination is on an island... it has it's own dock which affords guests the ultimate in flexibility. It was the main reason we elected to overnight there. My son and I only had one night for the fishing trip in our own boat over father's day weekend so it was not a deal-breaker we had to book 2 nights. The simplicity of motoring up after a day on the water with all of our gear and the convenience for being up early to catch the right tide was a perfect fit. Wish we had 2 nights to stay and have better luck with the weather... and the fish, but we will be back. Thanks Janet!

We had an amazing holiday weekend at Dave and Jenny’s cottage! They were always so quick to respond with any requests we had! The cottage as perfect and just like the pictures. They literally had thought of everything! The sunsets were absolutely stunning and it was truly the most relaxing time we’d had in a while! It was just what we needed !

Loved the cottage! Quiet, peaceful, and homelike, just what we were looking for. We particularly enjoyed the fishing and crabbing- would definitely return!

This was the best family getaway we had in years. Beautiful property with amazing access to nature. Host was very responsive and available. Will definitely come back!

I had an amazing stay for my wedding weekend. The view of the water was unbeatable and the brand new outdoor furniture was great! Heather was very responsive and it was overall a great place to stay!