Vacation rentals in Chestertown

We loved our stay at the cottage. Everything was clean and well maintained inside and out. We especially loved the gorgeous surroundings. The property was beautiful and peaceful. We enjoyed daily swims in the pool and time at the dock. Robert was a wonderful host and made everything very clear and easy as well as was easy to communicate with. We couldn't have asked for a better get away. Chestertown is adorable and fun to check out. We hope to return in the future.

Isaac was a great host! He responded very quickly any time we had an issue and the location and home was perfect for our stay! Overall 10/10.

This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.

Beautiful apartment with great touches from Becky and very clean! Becky was very accommodating and communicative. We loved our stay!

Great place! Really cool location that makes you feel part of this unique community. We were in town for a family wedding and it was perfect. Our host Donna was exceptional (and friendly). We need to find a reason to go back soon!

Both hosts were so responsive to my questions. The house had everything I needed truly for my guests and I to enjoy ourselves. The surround sound system was such a nice touch. All the bathrooms were nice and the kitchen had everything in terms of utensils to cook fab meals. It is in the very rural side of Maryland and there isn’t a ton to do, but wow the house was beautiful and beyond peaceful.

The house was very easy to find and get in to. The neighborhood was walkable and grocery store was super close. The views were spectacular watching the ospreys dive for fish along with the great blue herons and numerous songbirds. All beds were very comfortable and the kitchen was VERY well appointed. We will definitely come back for a longer stay!

Rebecca’s apt was exactly what I was hoping to find for the few days I was there. It was very quiet and comfortable and an easy commute to the event I was in town for. Rebecca was extremely responsive to my questions and very welcoming. The apt is very cute and very clean and comfortable. I had my little dog with me and he is elderly and he was very comfortable there as well. I’d definitely stay there again!