Apartment vacation rentals in Kent County

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

Our stay was terrific. Everything was as described and more. Kimberly thought of Everything. Kimberly was very proactive with advice on things to do and places to go. The place was very clean, updated and comfy. If you are looking for a quiet getaway with great amenities, this is a winner. We definately will be back !

We loved it. Of all the places we stayed, it was at the top. Could not have had better hosts who were responsive but very friendly. Would recommend to friends as we have already have done. Very comfortable and had everything we needed. Close to restaurants and other places of interest.

My partner and I had a lovely weekend in Chestertown at Beth & Bob’s cottage apartment! They really went the extra mile to make sure we felt welcome and had everything we needed. There were so many thoughtful touches to make sure we were as comfortable as possible. We also loved walking through their beautiful garden. I’m certain we’ll be back again, and we highly recommend this cozy and relaxing spot!

This spot is a very utilitarian unit but perfect for my dog and me. Very easy to walk to town, the bed was very comfortable and it was great having access to the backyard.

Katie was an amazing host and communicator! We loved the space and it was exactly as it was shown. The location was unbeatable. Would love to stay here again!

What a lovely place to stay, in a lovely town, taken care of by a lovely landlord. Appreciate everything-will return!

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!

It was an extremely lovely apartment overlooking the beautiful Chester River! The apt was spotless, warm, inviting & had lots of amenities. Walter was beyond helpful: he rescued me when my rental car broke down out of town on the highway in the rain. You can’t ask for more than that!! Thank you for a wonderful stay!!

Our stay was terrific. Everything was as described and more. Kimberly thought of Everything. Kimberly was very proactive with advice on things to do and places to go. The place was very clean, updated and comfy. If you are looking for a quiet getaway with great amenities, this is a winner. We definately will be back !

We loved it. Of all the places we stayed, it was at the top. Could not have had better hosts who were responsive but very friendly. Would recommend to friends as we have already have done. Very comfortable and had everything we needed. Close to restaurants and other places of interest.

My partner and I had a lovely weekend in Chestertown at Beth & Bob’s cottage apartment! They really went the extra mile to make sure we felt welcome and had everything we needed. There were so many thoughtful touches to make sure we were as comfortable as possible. We also loved walking through their beautiful garden. I’m certain we’ll be back again, and we highly recommend this cozy and relaxing spot!

This spot is a very utilitarian unit but perfect for my dog and me. Very easy to walk to town, the bed was very comfortable and it was great having access to the backyard.

Katie was an amazing host and communicator! We loved the space and it was exactly as it was shown. The location was unbeatable. Would love to stay here again!

What a lovely place to stay, in a lovely town, taken care of by a lovely landlord. Appreciate everything-will return!

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!