Beachfront vacation rentals in Calvert 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++++++++++++++

Pretty home in a great location. You can just park your car and walk everywhere. Well stocked with books, videos and games. Brian communicated well and was very responsive. Recommended.

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 had a wonderful stay at Britta’s place! From the moment I booked, Britta was incredibly responsive—and quick to reply. The Elk Cotrage was the perfect retreat for us and we especially enjoyed the screened in outdoor deck. I would absolutely stay here again.

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

We had stayed there before and had a nice time so it was easy to go again!

This was one of the loveliest Air BnBs I’ve had the pleasure of staying at. The photos don’t do it justice. A warm, welcoming and cozy home, filled with sunlight and stunning water views from every window. You literally feel like you’re on a boat! Comfortable furnishings and beds, a super well-stocked kitchen with lovely dishes and decor, bikes, kayaks, gas grill… everything you could want. The Tilghman Island General Store was just a short walk through a lovely neighborhood with the friendliest people. Breakfast at Two if by Sea was amazing! And crab cakes at Gina’s on the Bridge were delish. My dog loved the stay too! Tilghman Island is a peaceful treasure in today’s crazy world.

This was a fantastic vacation rental- the kids’ favorite yet! You can’t beat the views and the proximity to the beach and shops. There is also a playground, library, ice cream shop, and pizza just a block away. The host had snacks, water, and milk available for us and the kids when we arrived, which was very welcome after a long car ride! And having beach chairs and beach umbrellas for use made our beach days so much better! We brought our paddle board and launched it off the local beach which was quite fun. Annapolis and DC are both far drive and, when we weren’t enjoying the local amenities, we found plenty to do just an hour drive or less away. I highly recommend this rental. Thank you for allowing us to rent your lovely home and we will definitely be back

Easthaven is a gem! We thoroughly enjoyed our time there. Something to do for everyone, indoors and outdoors. Really nice to have the SUP and kayaks available, as well as the crab pots. So many thoughtful touches, probably the most well stocked home we’ve stayed in. Definitely hope to return in the future!

We found Paul’s home very comfortable and accommodating. Paul was accessible when we reached out to him and he communicated well with us. It was a very nice location with a fantastic view of the bay, as we hoped for.

David and Wendy’s home was the perfect place for our family participating in and supporting the Cambridge Ironman with an easy walk to the course and to the Main Street. They went above and beyond accommodating our requests, since we were traveling with a two month old and a two year old. We were very comfortable and loved our evenings in the screened in porch and pool. We would love to stay at David and Wendy’s again.

My family and I stayed here for a week for our family vacation. We are a group of 8 (6 adults and 2 kids) and there was plenty of room for all of us. We barely left the house because with the beautiful view, dock, beach area, canoe, kayaks, hot tub, game room/ library, corn hole, and fire pit we all had plenty to keep us entertained. Everyone loved Mary & Shelly’s place, and it provided the perfect space for us to enjoy the river and each other’s company!

A cozy and quiet cottage right along the water. The kitchen is very well stocked. You can find any pot or utensil you may need. The best part of the cottage is the sun room, it was a great place to enjoy a glass of wine in the evening or enjoy a cup of coffee in the morning and soak in the sparkling water and peaceful surroundings. A peaceful spot away from everything, but a short 15 minute drive into St. Michaels. The road to the cottage is a bit rough, a small car has to navigate it with some care.

great location and very clean!

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!

A great place to enjoy a long weekend at the Eastern shore in Maryland.

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.

This is a newly renovated gem, walkable to North Beach boardwalk. Spotless and great outdoor area. Host was very responsive and we would highly recommend. The beach is super close to the DC metro area (one hour) and perfect for young kids since the water is calm, warm, and most importantly shallow. We’ll be back!

Great neighborhood. Close to the water.

The location is peaceful, private and gorgeous. It is as just what I wanted and needed for my 50th girls getaway! We loved every second there! The beds were comfy, location was quiet, the water and outdoor amenities were perfect! We easily made it work for 6 girls and one bathroom- which was no issue at all! A storm came through and left us a beautiful double rainbow! There is a resident bunny who comes out mornings to forage. We spent most of our time relaxing by the water with the chairs, loungers and umbrellas! My daughter and her friend played safely and happily on the shore by the water and my friend and I kayaked over by the cliffs. It was a perfect weekend at Colin’s and we plan to come back again! What fun and relaxation we had in a private setting with very nice neighbors. It went BEYOND our expectations! Colin was always kind and super timely when responding to any needs. We will be back! 💓🙌🏼

Perfect getaway spot on North Beach! Location, location, location!! Walkable to boardwalk, pier, great restaurants and shops. Although it is an older home it has been nicely renovated and we especially loved the front porch where we spent our time relaxing in the morning before we headed out for the day. Extremely responsive host! 5 Star Stay! We would not hesitate to book again!

This little Chesapeake Cottage is a gem. Located on the border of restaurants on 7th St it's also a stone's throw to the Bay. I could see boats in the Bay while chilling on the wonderful porch. Everything is bright and beachy in the kitchen area. The LR is roomy and cozy. The front porch is a beach house must; it's bright and airy after the heat of the day. I slept soundly in the comfortable bed and luxuriated under the showerhead. I've visited North Beach for over 30 years living locally. I've always dreamed of renting a little cottage close to the Bay and staying a week. Mission accomplished with resounding success. Thank you Heather and Jan!

We had a beautiful stay. It was exactly what we needed.

This was a cute little home to stay at over the weekend. Only downside was having to pay for beach access. But the house itself was very nice and had all the kitchen items we needed. Would stay again.