Search Vacation Homes in Chestertown

"Very clean, great location - easily walkable for a USNA reunion to stadium and alumni center!"

"What a wonderful home, spacious just beautiful! But the view of the bay was everyone’s favorite, we spent 98% of the time outside only inside for eating and sleeping. The grandkids didn’t pick up and electronic device the entire time, they played basketball, fished, cornhole, counting boats. The only time a TV was turned on was to watch Big Blue Madness and the Kentucky/Vandy game (we’re from Kentucky). But if you like TV there is one in every room! This home is very well stocked with everything...

"Porch is filled with cobwebs. Steps inside need a lot of improvement. Inside was very clean, if dated. However I was pleased with the updated shower, refrigerator, kitchen. No tv made the down time lonely. Netflix did not work, nor did dvd player. For me I needed a much more closer bathroom on the second floor. Getting up 3 times a night to use bathroom & navigating those poorly constructed stairs was scary. I did not want to stay in the single bed right by front door. SUZANNE was very...

"I rented this property as part of a surprise weekend getaway for my son's 16th birthday. Our party included 2 adults, 4 teenage boys, and 2 small pups. To start, communication with the host, Ray, was superb! He has a great personality and is very easy to talk to. Prior to our trip, he gave me a complete overview of the property, its location and better driving directions than any of the map apps. Our set up was a little complicated because I was surprising my son and we had the majority of our...

"We were in town for a sailing event and the house was in a perfect location for us. "

"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"

"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."

"The house is spacious (more than the photos may lead you to believe), with numerous gathering centers inside and out. My guests enjoyed the dock at sunset and the fire pit by the water. The patio under the house had a charcoal grill and ample space for tables and chairs. Though our weekend had perfect weather, the covered patio made the place "weatherproof" had it rained. There is tons of parking, and a beautiful view over the water. The Host was readily available via VRBO messaging, Usually...

"Pretty house in a lovely location. Everything went very smoothly."

"The property was excellent location for our purposes of exploring the area. For future reference you should update the ‘amenities’ to clarify that the coffee maker is a Keurig type and not traditional. Also having throw blankets handy for cool evenings on the deck would nice. "

"Good"

"We stayed at this place for a family wedding at the nearby beach club. In addition to be a convenient location, the views from the house and property were stunning. The style inside the house was quite eclectic which gave it wonderful charm. Coming back at night gave us fits trying to find the driveway but that was a small price to pay for such a great house. "