Apartment vacation rentals in Kent County

It exceeded my expectations based off of the pictures I had saw. Super easy check in and they even left a handwritten card and some snacks for us. Thanks Josiah for the welcoming touch!

Comfortable beds, spacious layout, great shower and great scenery

We were charmed by the comfortable design of Kimberly’s place. Great a/c, fully functional kitchen, lots of extras (water, snacks, oil, seasonings, coffee, tea, creamers, etc). Spacious for the two of us, this is a small apartment, with kitchen, LR with table, bedroom and bathroom. Everything is like new. We initially had some problems with the WiFi, but Kimberly and her husband kept working on it until we found a solution. Excellent communication! Close bike ride to town, beach, restaurants in walking distance, beautiful spot.

Tony and Tina’s home was very comfortable and peaceful. They were very pro active in communicating and accommodating in checkin and check out. They made sure the light was on as we arrived late. Very comfy bed!! Very nice!

What a great place to stay! Everything I needed, beautifully and thoughtfully set up, a block from downtown, and an pleasant walk (or drive) to the Chester River right through the historical section of town, especially in the morning or early evening when everything is peaceful. Many thoughtful touches upon arrival - right down to biscuits for the dog - and helpful things like a basket of travel sized toiletries in case I'd left something behind. The hosts were easily available if needed but explanations were clear and everything intuitively set up, so I didn't need a thing. Thanks, Beth and Bob!

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

Deborah was a great host! Very communicative and helpful when we had questions. The contactless checkin could not have been easier. The place was super clean and had the things you need to be comfortable. We loved that it was right in town and very walkable to restaurants, grocery store, West Marine and the hardware store. It’s the perfect spot for boat cruisers who have a boat on the hard and can’t live aboard while doing the work.

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!

It exceeded my expectations based off of the pictures I had saw. Super easy check in and they even left a handwritten card and some snacks for us. Thanks Josiah for the welcoming touch!

Comfortable beds, spacious layout, great shower and great scenery

We were charmed by the comfortable design of Kimberly’s place. Great a/c, fully functional kitchen, lots of extras (water, snacks, oil, seasonings, coffee, tea, creamers, etc). Spacious for the two of us, this is a small apartment, with kitchen, LR with table, bedroom and bathroom. Everything is like new. We initially had some problems with the WiFi, but Kimberly and her husband kept working on it until we found a solution. Excellent communication! Close bike ride to town, beach, restaurants in walking distance, beautiful spot.

Tony and Tina’s home was very comfortable and peaceful. They were very pro active in communicating and accommodating in checkin and check out. They made sure the light was on as we arrived late. Very comfy bed!! Very nice!

What a great place to stay! Everything I needed, beautifully and thoughtfully set up, a block from downtown, and an pleasant walk (or drive) to the Chester River right through the historical section of town, especially in the morning or early evening when everything is peaceful. Many thoughtful touches upon arrival - right down to biscuits for the dog - and helpful things like a basket of travel sized toiletries in case I'd left something behind. The hosts were easily available if needed but explanations were clear and everything intuitively set up, so I didn't need a thing. Thanks, Beth and Bob!

We found this beautiful place when we needed a dog-friendy rental for our large dog while visiting our son at college. The rental is in a fanatic location, a very short walk to the waterfront and downtown Chestertown and its great shops and restaurants. The rental was immaculate and very comfortable. It had everything we needed. The backyard was more private than we thought and our dog enjoyed playing fetch in the back. The bedding was comfortable and relaxing. The host was very responsive and helpful. Great experience! Thank you!

Deborah was a great host! Very communicative and helpful when we had questions. The contactless checkin could not have been easier. The place was super clean and had the things you need to be comfortable. We loved that it was right in town and very walkable to restaurants, grocery store, West Marine and the hardware store. It’s the perfect spot for boat cruisers who have a boat on the hard and can’t live aboard while doing the work.

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!