Search Villas in Chestertown

"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...

"Great weekend with friends in this beautiful home. Plenty of space for the 14 of us. Indoor pool/bar area was the perfect space for us to hang out together."

"We had a wonderful time at Blake House with our extended family. Lots of room for everyone and we all loved the property, pool and offerings. The elevated welcome package, yoga session (for 11 of us!) and Chef Erica and team dinner were such incredible experiences. It was a perfect vacation. Highly recommend!!"

"We are two families with small kids (ages 1-5) from the DC area, and we thoroughly enjoyed our weekend. It took us exactly 2 hours to drive from the DC suburbs which made it very doable as a weekend trip. Instacart delivered groceries, which we appreciated - at other more rural VRBOs that we’ve stayed in it requires 30+ minutes round trip to the nearest store if we forget something, so it was nice to avoid that. The pool was in great condition and we swam in it 3x a day, which thoroughly tired...

"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...