Search Vacation Homes in Chestertown

"The house is absolutely beautiful and we fully enjoyed our time ! Thank you so much!"

"Wow, what a fantastic property! We had 14 adults (7 couples) travel in for a Cousins Reteat and could not have been happier with the appropriately named Terrace on the Lake. The property is very clean and well maintained. We used all 8 bedrooms, which were very comfortable. The two fully equipped kitchens made food storage and meal time prep easy and interactive with the upstairs kitchen being open to the large kitchen table and living room area. The location on the lake and view is spectacular!...

"Enjoyed our stay. Relaxing and comfortable. Will book again next year."

"Excellent location! Minutes to restaurants and shops! Very nice rental! "

"We were looking for something for our “baby moon” before I go back to work. We had a dream checklist and this home checked off everything on our list. We brought our 3mo old and our dog and had a peaceful weekend enjoying the hot tub, the Blackstone, and the cozy fireplace. We had some questions that were answered immediately. Can’t wait to go back with friends when it’s warmer not enjoy the pool and yard more! Love love lovd"

"The host was incredibly responsive to our questions and any issues we encountered. The house is perfect for gatherings with friends and family, offering plenty of activities on-site for all ages. The kitchen is well-stocked, making our stay enjoyable. We had a wonderful time!"

"Fantastic!! Cozy!!! gorgeous views! The whole experience was wonderful. Cannot wait to go back. Owner was very responsive!"

"The house is even better in person. So many beautiful amenities and we really enjoyed having a small shallow area to swim in. Ducks would often come right up to the dock. Beautiful firepit and grill area. Very accommodating host. We rented a boat and loved having a dock to keep it at overnight. It was a perfect house for a family vacation!"