Vacation rentals with a kayak in Kent County

Ina was a great communicator - from initial contact, instructions for the house, to checkout! She couldn’t have been better. She was quick to respond and very helpful, which made everything super easy. The house had such an amazing view! Our water-loving dog found the river within 5 mins of getting out of the car!! Great amenities (incl. kayaks, life vests (even for the pup!), well stocked kitchen, bed linens, comfy beds and furniture, nicely decorated, and clean)! It was an easy ride to town. We went to get a bit of a respite from our busy lives for a few days in the off season, and the surroundings were just what we needed. One downside was that the utilities (refrigerator and heat) are rather loud when they turn on, so if you’re a light sleeper, you may be bothered. We were awakened a few times, but the rest of the positives made up for it!! Great spot!

Great place, we had a family get together and we had a very peaceful weekend. There were so many places to hang out between the porches and dock-side area, big living room and huge dining room table. Very tranquil, I was thoroughly pleased with the home!

Our family had a lovely Thanksgiving stay at Martha’s Airbnb. The house was well-designed, the location was convenient, and we enjoyed the games in the basement and the beautiful views. The pizza oven was a fun touch, and the kitchen had everything we needed to prepare a great Thanksgiving meal. We also appreciated the nearby nature preserve and had fun playing Catan and putting some jigsaw puzzles together. Martha was very accommodating, even letting us extend our stay briefly when we ran into an issue unlocking our car. It was a great experience overall, and we’d definitely recommend her place.

We had an incredible stay here! The house is so spacious and has so many places for people to gather. It was the perfect place for our little retreat. Hal was a great host and super responsive and kind. The views were also so beautiful. Can’t wait to return!

Our stay was very comfortable. The place had everything we needed to cook as well as for kids to play. The inflatables, toys and pool table were hits with our group. There are two beautiful piers with amazing sunset views at the back of the house. The walk in the community was pretty peaceful too. Landon was responsive. We had some trouble locating the lock box at the front door that resulted in trouble during the check in. You need to press a button to see the lock box on the door. We realized late that we were using the wrong lock box.

We loved our stay! The house is so cute and even better than the pictures! Everything was top notch and we greatly enjoyed the luxury amenities and little touches that made a difference, like chargers throughout the house. We loved watching the birds!! Jessica was so kind and responsive!

Super comfortable cozy apartment! We loved the local and the view. Thoughtful touches of snacks, water etc. made a nice welcome. We will definitely want to come back next year. After each evening event we said "Let's go home" doesn't get much better than that. The bed was entirely wonderful, comfortable and warm. (Not easy to find a comfortable bed when away) Thanks to our host -Misty

My husband and I along with our dog Cash had a wonderful stay at Tom and Jen's place. It was very spacious and the view was spectacular. The fenced in yard was great for our dog who loved meeting and playing with their dog. Tom and Jen chatted with us when we first arrived and made us feel very welcome. The neighborhood was very peaceful and we really enjoyed taking our dog for walks during our visit. Everything was perfect! We would love to stay there again next time we're in Chestertown.

Pros: absolutely beautiful setting, great fire pit area, nice wood burning stove, plenty of wood, blankets provided for outdoor fire pit, the area is great! Went to Crow vineyard and winery it was absolutely amazing, The Kitchen for Sunday Brunch and The Granary for oysters. We actually did a Scavenger hunt on Lets Roam App that was lots of fun. The weather rained for 2 days but we we got 1 day by the fire pit which was awesome!!!! The only thing I would keep in mind is the steps to the water are very very steep. Might be hard for kids or out of shape 50 year old like me.