Beachfront holiday rentals in St. Mary's County

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 had an amazing stay at Ryan’s place for our Father’s Day weekend fishing trip! Ryuan was a fantastic host—very accommodating, responsive, and made sure we had everything we needed. The home was just what we hoped for and helped us create some wonderful memories. Thank you for making our trip extra special, Ryan! Would absolutely stay again.

Loved it so much great view and everything!

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.

We had a great time at Nicholas and Dana's place! It was both fun and relaxing. We really enjoyed the little beach, the dock and the kayaks. We caught some catfish and one tiny crab in the crab trap (and threw everything back in). It was nice to have the firepit and hot tub to use too. And, the kids really liked being downstairs in their own space. The only issues were that the key pad wasn't working to get in to the front door which was frustrating after a long drive and the grill was very slow to heat up and probably needs to be replaced. Overall, this home was a really good choice for us and we would stay again when visiting family in the area.

Super fun place really peaceful The house was super nice. I loved waking up in the morning and seeing the sunrise.😁🫶🏻

Have now stayed here twice and love it so much we just booked our next visit. It's a lovely and comfortable home!

Our stay was great. The house is located in a quiet friendly neighborhood. The views are amazing. The house is very comfortable and so relaxing. Loved that three bedrooms each had a bathroom. The hosts were wonderful and very responsive.

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!

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!

The house is beautiful and very large. Three families with kids had plenty of room to spread out. The views are just as pictured and the finishes were all high end. As we knew from the listing, the pool was right on the deck with no fence, and this was stressful with our younger kids (as were the stairs). This wasn't a surprise but something to keep in mind if you're traveling with small kids. As another review pointed out the house feels out of place in the neighborhood. Melanie was very responsive and helpful and we had a great trip.

We spent some wonderful days in this house, it's spacious, beautiful and clean. We enjoyed the kayaks, paddle boards, jacuzzi, and the spectacular views of the river. Frank is an excellent host, very responsive. We definitely recommend this house for a relaxing and fun stay.

Terry’s place was just what I was looking for. This quiet neighborhood is located on the beautiful cliffs along the Chesapeake. The beach was truly magical. It was so peaceful and I enjoyed walking along and collecting fossils and shells. Terry was such a friendly and gracious host making sure we had everything we needed. The room was clean and the bed was very comfortable. She let us use her space and guided us to many activities and attractions nearby. We really enjoyed hiking the nearby wooded trails as well. She even took us sailing! We look forward to visiting Terry’s place again!

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.

We have stayed here twice now, both times in June. Will definitely be making a yearly trip of it, as we enjoyed it enough for many return trips. For our purposes, having a remote & very quiet location, with plenty of room for the dogs to run around, it is a perfect fit. Fenced in yard, private beach and again, not many people, if any around. As far as the home itself, it is very roomy, very clean and free of any clutter so getting settled in feels great. If you have kids, dogs or both, this is the perfect family getaway spot. Highly recommended!

First off check in was a breeze. The house and amenities were just as Frank described even better! The house was stocked well enough with plenty of towels for the beach and bathrooms and blankets. The kitchen was stocked with basic products to start the week off which was a huge help! The house itself has more than enough space for a large family to spread out. The large family sunroom and dinning area was a great gathering point and having 2 living rooms with tvs made sure the kids had their own space as well. The loved the 90’s Nintendo system! The mattresses in the master and the full in 2nd bedroom are extremely comfortable! Frank makes sure that there is more the enough outdoor toys like kayaks, SUP’s and life vests. We used them all week long! Montross crabs were fantastic. Our favorite part about franks place is being able to bring our dogs with us. Weather can change quick in the area but made for a great memory being able to see a tornado/water spout over the river!

Perfect Lake Side Vacation Spot!!! My friends and I spent the weekend and we absolutely loved it! The home is beautiful and the surroundings are so serine. Perfect place to get away and spend pleasurably days participating in outdoor activities like fishing, grilling and watching the sunset. We loved our stay so much we are already planning our next trip to the wonderful spot! Tim is an amazing host! Check in and check out were a breeze, he kindly checked in on us and was always prepared to help facilitate an enjoyable stay. I couldn’t recommend this listing any higher :)

Nice little getaway on St. George’s island. Very affordable.

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!

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 think this is my 5th time staying there. Always thinking of my return visit before even leaving!

We had a wonderful long weekend here! The house is well-equipped and David was even able to secure fishing and crabbing gear so our two kids could try to catch dinner. It is a quiet street of cottages with friendly neighbors in a gorgeous location - the view is so calming. We enjoyed exploring the local area (love the coffee shop and brewery in Montross), kayaking, swimming, and relaxing on the big screened porch. A feature here that you don’t always have at the shore is a great sandy beach! Can’t wait to come back for another getaway.

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!

We loved our experience here. The home was thoughtfully appointed and extremely clean. The view was stunning and very peaceful.