Search Holiday Homes in Chestertown

"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."

"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "

"Crystal responded very quickly (within an hour) to provide me with check-in instructions. The place looks exactly like the pictures, smelled amazing, and was very clean. I had a small get together for my partner’s birthday and we played pool as well as card games at the poker table. Everyone kept saying how much fun they were having at her place so I definitely recommend. 10/10 Crystal thank you so much!"

"The house was clean and the beds were comfortable. "

"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."

"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "

"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "

"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"

"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "

"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"

"Our stay was absolutely wonderful! The amenities that Matthew provided were great -- there were mints, lollypops, and granola bars for each of us upon arrival. The space is incredible! From the Master Suite with a king-sized bed that was adjustable to the other bedrooms that were comfortable and cozy. Also, we loved the small details, like the beautiful paintings and decorations, plus the "Baltimore Bucket List" to check-off. Everything was clean and neat, and anytime we had a question, Matthew...