Waterfront holiday rentals in Calvert County

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!

What a calm and peaceful private retreat! My fiancée and I spent a couple of days enjoying the brisk bay breezes and beautiful sunsets at Vickie’s. Everything was exactly as advertised and Vickie (and Scott) are true treasures—extremely responsive and thoughtful hosts who want you to have everything you need. Plus, their knowledge of the area gave us a great introduction to Leonardtown. So much more to the area than we thought! Whether birdwatching from “the best view on the block” or reflecting on the glider by the bay, we loved every moment of quiet and can’t wait to visit again. Thank you!

Brittany’s waterfront home in Colonial Beach was a beautiful and peaceful retreat for me, my husband, and our 2 year old son. The space is beautiful and clean and offers lovely views of the sparkling water and beach just steps from the front door. We loved having beach days and visiting the pool, and nearby restaurants made it easy to grab lunch and dinner after a busy day in the sun. The in-unit washer and dryer made it easy to clean our swimsuits and stay on top of laundry, and the fully stocked kitchen made cooking a breeze. The porch also provides a nice space to take in the views and the sounds of waves crashing in a private and peaceful retreat. We loved visiting Colonial Beach and would happily stay at Brittany’s home again!

This was unanimously our family's favorite AirBnB! Dana and Mike are the dream hosts! Our accommodations prior to our scheduled arrival were cancelled last minute and they immediately jumped in to help. They were extremely considerate of our privacy whilst being right next door but also quick to respond when we reached out to them. We could not of asked for a better mini-vacay in the middle of our travels. The beautiful surroundings, welcoming accommodations and hosts, attention to detail throughout amenities and decor, and impeccable cleanliness were top-notch. We really enjoyed the heated pool too. The kitchen and grill were easy to navigate and stocked with all essential items needed to prepare meals. The Monocle Meat Company and Lovepoint Deli & Wine are great local shopping options. If cooking is not in your plans, Avanti has amazing pizza. Thank you Dana and Mike for going above and beyond to make us feel at home! Heron Roost is now our must stay place when visiting MD.

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.

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.

We came in very late our 3 hour drive turned into 4 1/2 due to severe thunderstorms and heavy rain. It’s was our safe harbor. Solomans island is very beautiful. Unfortunately we misunderstood the check out time on top of we were waiting on a boat surveyor. The place was clean and close to many attractions and shops.

Teresa’s A-frame was incredible! With the screen doors in place, we got a really nice breeze with the sounds of the ocean and birds. The beds were very comfortable and the whole place was clean. The beach is was a short walk away with wildlife and beautiful views. We would love to return our next time we’re in Maryland!

It was a great stay and a perfect location for our quick family back east. It was very comfortable, clean and a the right size for our family of 4. It was nice to have our own place to stay and not to far from our family. We didn’t spend much time in the town but it looked cute with shops, cafes and restaurants. We had great communication with Maria, she was very quick to respond. Thanks for a great and comfortable stay!!

We returned to this gorgeous home for a second time this summer for a full week’s stay. Not only is the home, landscaping and views beautiful, the house is well equipped with everything we needed for a very comfortable stay, especially the kitchen. We enjoyed finding shark teeth on the private beach, relaxing in the hammock and taking drives into town which is just a short trip away. Nicholas was a super helpful and responsive host. Thank you for your hospitality and sharing your beautiful home! We’ll be back next year!

This was our second year in a row visiting Julya’s place! Our family loved it so much last year we booked as soon as we could for this season. The house was just as beautiful as we remembered, the kids even said it felt like home the second day. All the thoughtful things included are so nice (blackout shades for the kids, all the kids kitchen stuff, extras for all usable items, beach items). And we love the location! Easy to get to activities, we very much enjoyed the marine museum, the Imaginarium, fishing on the shea-d-lady, and sailing with Sail Solomons. Island Hideway was huge hit with the whole family for dinner. The house is an easy walk to the beach and the view is so cool, feels like a beach treehouse. Will hopefully be back again next year (if not at the end of this season!) 😁 Thank you Julya!!

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!

Dale is an incredibly proactive and helpful host. He checked in with us several times to ensure we had everything we need and went out of his way to meet us on our schedule to check in and show us around. This is a great spot to relax and look at the ocean or an easy commute to Solomon's Island and all its amenities. You also get access to the community's private beach, which is beautiful and a real asset!

We had a great stay here. Beautiful views of the water. Hosts were quick to respond. Good WiFi. Large deck with teak table and weber grill. Easy walk to water access. The waterfront is the best I’ve seen on the Bay. Sandy with shady and sunny spots against the cliffs. From the water access, you can walk in one direction to the limestone cliffs for shark tooth hunting. The other direction goes all the way to the marina. We hope to stay here again.

We had a very enjoyable stay at this perfect River House. The place was warm and comforting, with some of the most amazing views you can find. We arrived shortly after check in time, and easily let ourselves in with the lock box code & key. Everything inside looked just like the pictures, and we weren't disappointed! If you're looking for some beautiful river views, right on the water, with your own private water access and dock, this is the place for you. We were in town for a wedding a few houses down, and this place couldn't have been any better for us. We were able to walk to & from, which was a huge bonus for after the reception...Cheers :) We enjoyed eating out a couple times in town, and really liked Brick Wood Fired Bistro & Traders Seafood Steak & Ale. We would highly recommend this property for anyone looking for a peaceful river stay, and will surely return someday in the future! Thanks for your hospitality!

Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.

We had an amazing girls weekend in large part because of how beautifully the rental was decorated, the amenities that came with it and its amazing location! We all agreed we will be looking at renting this location again next year!

Condo was in a perfect location in North Beach area. Loved walking boardwalk and walked 5+ miles daily. Felt very safe in the area, everyone was so friendly. Mexican restaurant and Baia were fantastic. Very peaceful. Condo definitely worth the money. Host was very responsive and let us check in early and was quick to reply to any text questions. Loved the view!

The host went above and beyond to support and welcome us. Some personal attentions and help securing extra umbrellas were much appreciated! The place was perfect for our needs, beautiful view, super practical with equipment and amenities, as well as access to the charming downtown Annapolis. It being Naval Academy Commissioning Week, we didn't have much time to interact with the host over the platform, who wanted us to check-in and out via texts and share additional info, but since everything went smoothly, we didn't really feel the need either. Commissioning Week prices are pretty high: they reflect the high demand for lodging, so it was fair. Just make sure you don't book that week if you don't have to attend a graduation :) We would gladly come again!

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.