House vacation rentals in Kent County

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.

The Creek Cottage at RCF is nothing less than amazing. This is the perfect getaway for privacy, peace and nature. We saw deer, foxes, fish, birds and tons of butterflies. The scenery is so beautiful and serene. The house was just enough space for the 5 of us and our dog - who loved sitting on the enclosed porch to watch us at the pool. The pool was perfect, the river was beautiful and it was nice to just sit and watch the scenery. Bryan, the property manager, was also great and suggested we try out the Crab Shack in Easton - these were the best crabs at a price we couldn’t believe (we got a bushel)! The first floor is fully accessible for those with special needs, but note that the bed sits high so a step stool may be needed. Also, beware of the horse flies - they can be pretty aggressive and intimidating, but we found ways to manage. We certainly loved our family staycation at the Creek Cottage and would love to come back in the future!

Been coming to Chestertown for the last 7 years and this one of the best spots. Perfect location on the river with awesome views from the sun room. Will certainly be back!

My family loved staying here. We had my 3-month old and my sister brought her 8-month old so we were looking for a place that could keep everyone entertained in one location and this place did just that! We enjoyed bird watching, collecting rocks on the beach, swimming in the heated pool, and watching the sunset from the hot tub in the evenings. This was also the first time I could say that the listing looked better in person than the pictures. Thank you Joni for letting us stay here! We made some amazing memories!

This was our 2nd year at Peaceful Waters. It is indeed just that! Peaceful! Perfect and beautiful location. Everything needed is there to assure a wonderful carefree stay. The place is well stocked, clean and is just as it reads and appears! My group of 16 loved the place AGAIN this year. Hopefully, planning to go back next year. Matthew and Rose are great to work with! ❤️

it's beautiful and peaceful ❣️ place to visit. all my family love it and Martha is a great host. I appreciate it 🙏 hopefully I'll visit it again

My family and I celebrated Christmas here so we could all be together… The location was perfect on the water and very close to where my parents live. The living room and dining room were actually bigger than the pictures showed. There were eight of us and a dog plenty of room.

The house was perfect for staying in the area for a friend’s wedding! The house was comfy and well stocked with everything we needed. Virginia was super responsive and so helpful- we lost our car keys the morning we were supposed to leave and she was very accommodating! Would definitely come back- curious about the pool in the summer 😎 Was within running distance from a trail and a beautiful nature preserve.

Karin and Andrew’s place was wonderful! The pictures represented the home perfectly. We were in town for our son’s wedding and 8 people comfortably stayed in the main house and then we had 2 more in the garage apartment. Both the house and garage apartment were clean and clutter free, everything is labeled and easily found, along with a binder full of instructions and recommendations. Karin left us a welcome to their home message that was personalized for our visit. We stayed on Halloween and a bowl of candy was left for us in case we had any trick or treaters. The house is easy to find and access. Karin was proactive in messaging me and quick to respond to any inquiries. Our family enjoyed our stay and all would highly recommend this home.

This house was perfect for our annual girls weekend! Gorgeous decor that looks brand new. Spotless kitchen equipped with everything we needed to prepare meals (even a crock pot). Plentiful dishes, glasses, and pots and pans. Furniture and bedding was so comfy and the porch was our favorite place. Peaceful and quiet - even woke up to a bald eagle sitting on a branch outside my bedroom window. We traveled 30 min to the Farmers market in Chestertown on Saturday and had great Indian food in Middletown. We all agreed we would come again.

Our Moms' group completely enjoyed our annual "Explore Maryland" getaway at George and Meg's lovely home in Rock Hall. The house is beautifully decorated, very comfortable, and extremely well-equipped. Great library, games and puzzles, too. George left a comprehensive list of suggestions for us to try, including restaurants and shops in this charming and friendly small town. Don't miss sunset at the beach! It was a wonderful adventure and a relaxing and fun weekend for us.

This house was the perfect spot for our family over Thanksgiving! This home is spacious and incredibly charming. We had a nice couple of days making memories in this special place.

Great stay! We will be back again.

We had the most wonderful weekend stay at this charming home while visiting our college son! The location couldn’t have been better—just a short walk to downtown and just a bit longer to the campus, making it super convenient for us. The home itself is absolutely pristine, with beautiful and comfortable décor that made it feel like a true home away from home. We loved spending time on the front porch, watching the world quietly go by—it was so peaceful and relaxing. The beds were incredibly comfortable, and the home was wonderfully quiet, ensuring a great night’s sleep. It had everything we needed and more, from cozy amenities to thoughtful touches throughout. Teddi was an exceptional host—responsive, friendly, and always happy to help with anything we needed. We couldn’t have asked for a better place to stay during our visit. Highly recommend this gem!

Lovely house in a beautiful and peaceful setting. Well equipped kitchen, bathroom and cozy, comfortable bedding and beds! I recommend Diana’s place for a peaceful and relaxing stay.

Carey's home is beautiful and comfortable. I wanted to bring the back deck home with me! If you prepare meals, he has a fully-stocked kitchen at your disposal. His home is just two blocks away from the business district of Chestertown, making our stay fully walkable. Because it's a small town, though, it's very quiet. This home offers everything you could ask for.

We had a wonderful stay at this beautiful place. Our extended family and dogs thoroughly enjoyed the private and peaceful location. Bobs place was provisioned very well. We appreciated the numerous coffee cups, wine glasses, etc. it felt very much like staying with family. Lovely art throughout too.

This very lovely home was a perfect home base for our family vacation. It's a perfect balance between old world feel and everything you need from a modern home. As long as you're weary of the slightly-too-narrow entry gate, you'll definitely enjoy your stay

This place is so great for family gatherings! We stayed here with my sisters and their families and we all had room to spread out. They layout is awesome because there is plenty of space for everyone to do what they want: gather, chill, play, eat. The beds were very comfortable and the decor of the house is so cool. There were even fun games that both the kids and adults enjoyed. Chestertown is very walkable and we enjoyed going downtown to restaurants, ice cream shops, and the Cat Colloquium. (FYI for other guests- Some places are closed Monday and Tuesday.) We had an awesome time. Lee was a wonderful host, super friendly and responsive. Thanks for everything, Lee!

Brian’s place was beyond our expectations - absolutely beautiful, comfortable, and spacious enough for all of us! Brian was gracious in allowing us to have our son’s rehearsal dinner in his home, and we couldn’t have asked for a more beautiful evening! Priceless! The beds were comfortable, the kitchen was very well stocked and the children had a great time exploring the outdoors. Thank you Brian!

This was the perfect location to get some rest and relaxation. It was beautiful with big views of the Bay. Bird and boat watching while sipping wine on the patio. The house was lovely with gorgeous plantings. The welcome treats were a nice surprise. Our dogs loved swimming and running in the yard. Great amenities and a very clean house. Fun restaurants in town which had a Key Westesque feel to it. We hope to be back again.

Laurie's place was perfect to stay while in town for a wedding. The water is right down the street for peaceful/calming views. We will deftinely stay again if we come back to Rock Hall!

Beautiful older home. Off-street parking. You do have to walk up stairs - one bedroom is on the second floor and one is on the third floor. Lovely kitchen and sitting room. Perfectly located in downtown Chestertown. Very relaxing. Very comfortable. Would definitely stay there again!