Beachfront vacation rentals in Chesapeake Beach

Less than .5 miles from sand . The kids loved staying at the house versus a hotel ! Was the perfect spot to relax and go on the deck to hear the water . Would definitely go back for another vacation.

Sue’s place is a perfect peaceful getaway by the bay. Close enough to restaurants to enjoy a break from cooking, too! The cottage is as described, but the workmanship of the renovations are exceptional. The design and decor add so much to this cozy place. We’d be delighted to return!

We loved out time at this Bayside home. My boys spent outside upon hours at the little private beach, where the water doesn't really get deep for quite a ways and the waves were never very rough. it was perfect for them. we all enjoyed the hot tub, kayaks, comfortable beds. My personal favorite was the hammock right by the water, listening to nothing but the waves and the calls of the ospreys that made the area their home. Forget the overly built up touristy areas and give this place a try. You will not regret it.

Michelle’s place had everything we needed! The kitchen and bathrooms were well stocked, the living room and dining space were both really nice to use, and we loved the backyard area and hot tub! It was also a very close walk to the water and downtown area! We would definitely recommend:)

We had a great weekend at this cottage. Comfortable layout, great dock, and a beautiful view. We hope to return.

Beautiful house and beautiful view. Outdoor jacuzzi with the view is not to be missed! Gorgeous and clean home. The private site made it an amazing getaway from busy life. Thank you, we will be back soon!!!

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!

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.

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

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!

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.

Our stay Rick/Kevin’s place was fantastic. The property and setting exceeded our expectations. Everything was extremely well maintained. We loved staying in the lovely guest house which had everything we could possibly want. There were so many wonderful places to relax, from the screened porch to the pool and the amazing outdoor kitchen in the open air beach house. We loved floating in the pool while watching the big screen TV. The best of both worlds! We highly recommend Rick/Kevin’s place.

This place is really great. The house is as described and very comfortable, but the star is the yards. The back yard goes right up to the water, has a pool and a grill, and is large. The front yard is even bigger and has a lovely kid swing under a tree. Definitely a great place to come if you want to spend a lot of time outside playing or looking out over the water.

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!

Wish we could have stayed longer! We didn’t need to bring anything. All linens, paper products, towels, and kitchenware were provided. Right down to mosquito spray. picnic blankets, and s’mores. Charles was helpful, flexible, kind, and available. He was willing to give my kids and I an up close lesson on beekeeping. He has 5 well maintained hives on his property and was eager for us to come along checking in on them. It was very impressive! The property was beautiful, peaceful, and quiet. There are a few paths to venture out on. One lead to the private beach, another out to a close view of the bay. The deck was the show stopper. The view of the water was amazing. While sitting on the deck, there were hummingbirds, butterflies, and deer passing through. And we could see all of this from the comfort of the hot tub . The game room was a nice bonus. There was something for everyone: darts, poker, drawing, puzzles, movies, board games. I appreciate you sharing your cottage with us!

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!

T’s place was absolute perfection! It was beautiful, tastefully decorated and the homemade muffins and cookies were amazing! She and John were so lovely and accommodating. Relaxing on the dock on the river was a sublime experience as well! I really can’t say enough about my time spent there and if I’m ever in the area again I will definitely be staying at T’s! Why would you stay anywhere else!?

Second time staying at one of the cottages and can’t wait to come back! The area is so peaceful and serene - great DC getaway. If you enjoy hearing just the bay waves crashing and birds, beautiful sunsets, and panoramic views even from inside look no further.

We rented A Little Slice of Cambridge because of the Iron Man competition held that weekend. It was convenient to the venue...and allowed to walk to the competition and nearby restaurants. Pamela was a wonderful host...communicating easily. The rental was well stocked with toiletries, dishes, pots and pans and extras. The house was comfy and the beds comfortable. An enjoyable stay...unfortunately, we weren't able to stay for more sightseeing...although I did walk down to the Lighthouse and beautiful wharf.

We loved the house; cozy, nicely decorated, with many pieces of original art that really added character. The kitchen is well stocked for those who like to cook. The location right on the water was wonderful, and Nancy provided kayaks, which we took advantage of. Our dog was beside himself with so much room to run. Nancy’s daughter and family live next door, and we spent quite a few hours enjoying conversation and local knowledge with them. We would go back again.

Keith’s water view cottage is so beautiful and peaceful. My husband and I had a lovely long weekend stay with our little dog. Even with the storms that passed through the bay we felt extremely safe and cozy throughout our stay. Keith was very responsive and flexible with checkin /checkout. Would definitely stay again!! Thanks Keith !

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.