Waterfront holiday rentals in Maryland

We went to Southern Maryland to celebrate our 44th Wedding Anniversary as it was where we met back in high school. We were greeted at Tom & Michele’s place with a sweet chalkboard message, flowers and a nice little cake to help us feel special and celebrated. That was very kind. Their apartment is extremely clean and very comfortable. The backyard is absolutely beautiful and very relaxing. We didn’t need help with navigating the area as we grew up there so we spent most of our time visiting places from our youth. Tom & Michele reached out to us during our visit to make sure we were doing okay. We are quiet people and don’t require a lot of assistance so it was nice to be asked but we were good. For us it was nice to have a chance to spend quiet time alone together and Tom & Michele gave us that. Should we find ourselves back in Southern MD we would definitely stay there again. Thank you for a wonderful visit ♥️

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

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!

Vickie and Scott were so welcoming and friendly. Respecting our privacy, yet nice conversations on our way in and out. The views, pier, and accommodations were exactly what was pictured and described. We will definitely be back. Location was only 10 minutes from downtown Leonardtown. Beautiful!

Beautiful views of ocean from large sliding doors to patio! Clean house good value responsive host! Would stay here again.

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.

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

We enjoyed our stay at Michael’s place, and it had everything we needed, along with good communication. The hot tub was a nice touch!

We loved this stay! The lite house was very nice and renovated, while still maintaining original structure. The porches all around were great and the view from the master bedroom was stunning. Easy walk to small private beach. Town is about a 10 minute drive. We dined at Woodys and the Wellwood and they were both tasty!

It was perfect for what we were looking for. Location was convenient to Annapolis, but in a quiet area and right on the water. It was a peaceful and restful weekend!

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!

Dave's place is beautiful! Sunsets are breathtaking! The place is perfect for 2 or 3 couples. Great restaurants 5 minutes away. We loved The Fisherman's Inn, the food was fabulous, and a great value.

Wonderful accommodations for a relaxing visit to a beautiful island!

A wonderful stay at Stephen's place for our son's USNA commissioning. Although he lives in the 2nd floor, he was very respectful of our space - we hardly knew that he was there. He was very responsive when you needed him and helped us to host a gathering of friends and family to celebrate at his beautiful home on the water. Highly recommend.

This is a beautiful home in a serene setting. Although there was plenty of boat traffic it was I. The distance and not noisy at all. The home is furnished simply but there are many more amenities than most airbnbs including children’s equipment and toys! The host readily honored a special request! The pictures are not clear about the water access. It is not a beach, but a stairway. We still spent much time at the water’s edge, and sitting in those great Adirondack chairs!!

Bao was prompt at responding to questions. The home was immaculately clean and much more spacious than appeared in the photos. The price was worth what we paid. My family and I were quite comfortable and we appreciated the starter items included with the rental. There were ample cooking utensils and the appliances were clean and in excellent condition. We travelled from out of state and brought a suitcase with our own linen. Not ideal, but this was a much more financially prudent option than paying the linen providers $190.00 for sheets and towels. Overall, we thoroughly enjoyed our stay at Bao’s rental. We were close to restaurants and the beach and had a view of the water. We highly recommend this property.

Amazing views! We watched the sunrise over the ocean from bed. The bathrooms are small with not much room to store your toiletries, but otherwise the space was great for my partner & I. We had a wonderful stay!

My husband and I decided to go on a getaway last minute. We found Seth’s place and were able to book the unit for the days we had available. It was great and met all of our expectations. We have been to OC and Fenwick many times and knew this is where we wanted to stay. It did not disappoint and we hope to rent again in the near future.

Really enjoyed our stay at Stephanie's. Awesome condo that was clean, comfortable and roomy. Wonderful views from Living Room, Balcony and Master Bedroom. Close enough to the water to hear the waves breaking. Plenty of restaurants and shops close by. Definitely hope to be back!

This is my favorite place to stay in OC and I have been coming here for over 20 years. Great location, family friendly, Betty is a super host! Will keep coming here year after year!

Shiri was very friendly and she reached out to make sure we had her number. We travelled with a one year old and she fell asleep before we could check in and they were very accommodating. They had everything, a playpen and even had beach toys as we forgot hers. The place is beautiful and in the perfect location with great instructions from Shiri. You have the perfect view for sunrise and sunset, the sound of the waves is very relaxing. The beach is literally at your finger tips. We will definitely be coming back again.

I had a wonderful stay at Brooke’s place. Being able to listen to the waves crash from the patio was so relaxing. There’s also tons of wildlife you can watch right from the patio. I saw a fox two days in a row, as well as dolphins each morning. The place had all the amenities I needed. I would love to stay again! The only thing I’d do different next time is bringing my own pillow. Otherwise, a perfect getaway.

Loved our stay. I’d definitely choose this condo again!