House vacation rentals in Chestertown

House owners were extremely responsive and informative. House was well stocked , and a great location and view made the stay even better.

Beautiful house and property, great location, and the host was super responsive. Hope to return sometime soon.

The house was exactly as described and it was so easy to communicate with them as they responded to texts within minutes

We had a great stay at this clean, comfortable, convenient and cozy house. We were impressed by the attention to detail. Every time we needed something, it was there. The kitchen was fully stocked and had everything we needed to cook our Thanksgiving meal. We were close to Annapolis And had an easy drive to the museums of DC. We took several walks to the nearby beach, and enjoyed both sunrises and sunsets. We would definitely come back! Thank you, Peggy!

We had a great weekend! The host was incredibly kind and accommodating, making check-in and communication smooth from start to finish. The house itself was well-stocked, clean, and thoughtfully organized—perfect for relaxing with a small family group. We especially enjoyed winding down in the cozy living room and falling asleep to a movie after a fun day out. Would absolutely stay here again!

We really enjoyed staying here. It was a spacious home and we love the community. We were in town visiting family and It was so convenient being so close to family and friends. Very comfortable

it's beautiful and peaceful ❣️ place to visit. all my family love it and Martha is a great host. I appreciate it 🙏 hopefully I'll visit it again

The moment we walked in we fell in love with this place. Clean newly appointed kitchen, open floor plan, fireplace, pool table, big TVs, children’s games, toys, and wonderful view of Big Pond. Great for bird watching. Beds were great, everything labelled and organized very smartly. Quick response to communications. We cooked a big meal and the kitchen was nicely stocked.

Excellent house for a family reunion, spotlessly clean and very comfortable. It features a huge, well-stocked kitchen, nice mattresses and bedding, and is situated in a quiet neighborhood with beautiful nature. I will definitely return soon.

Kevin is a great host to us year after year! we love staying at his place!

Attention to detail both architecture and a fully equipped kitchen with spices etc Visually unmatched sunrise to sunset

- I wanted to have a nice getaway with my partner and couple friends since it was her birthday, this was everything I wanted and more and loved how comfortable and nice the home was. Will definitely be coming back in the future! Thank you Adam!

This home is worth it just for the beautiful views of the Chesapeake bay! It was a gorgeous space with plenty of seating for our family vacation. The master bedroom and bathroom were also a highlight for us. The large soaking tub fits two and the shower was amazing. It being winter we couldn’t make use of the kayaks but we loved the hot tub and there is a lovely park walking distance from the house. We drove into Annapolis and also spent a day in Baltimore as the house is in a great spot for driving to either. Can’t wait to check this place out in the summer!

We had a fantastic stay at Evan’s place. The cottage is beautiful and we really appreciated the lovely touches (fresh eggs, butter, dog biscuits). The property is beautiful and we enjoyed the calm waters of the bay and watching the ospreys. Highly recommend for a lovely and relaxing get away!

The cottage /house was peaceful on the edge of an inlet from the Bay. The patio was lovely. It was chilly so we couldn’t use the kayaks. The kitchen was very well equipped. The dishes, utensils, cookware were quality. The extra cozy blankets were nice. He responded to a request very timely. We enjoyed the stay very much.

We had a wonderful time at the farm! The house looked exactly like the photos, and the kids absolutely enjoyed getting up close with all the different animals. The place was spotless, and our host was incredibly friendly and quick to respond. The location is peaceful yet conveniently close to everything you might need, from restaurants to playgrounds for the kids. We would definitely choose to stay here again on our future trips!

Erin's place was a great place to stay in Annapolis. My family was in town for Commissioning Week at USNA. Annapolis is a beautiful town with tiny streets, so being at this location aloud us to walk to the Yard and restaurants. Would definitely stay here again when in the area. Thanks again Erin for your hospitality.

Kelsey’s place is incredibly special. The location is right in the center of downtown Annapolis, close to the water, shops and dining. For us being close to USNA was important in visiting our mid, and you couldn’t be any closer. The place was cute, comfortable and very spacious. But, the Kelsey as a host was impressive. We had a couple issues when we arrived, but she was communicative, incredibly responsive and handled it all incredibly professionally. We hope to stay at her amazing place again!

Excellent time staying here. Courtney was courteous and very responsive to our needs. Definitely a must use if ever in the area! Thank you Courtney!

Had a really great stay for three nights at this lovely home in Edgewater. The house sits on a corner lot with wonderful views of the bay. The neighborhood is safe and cozy. Lots of friendly people out walking and enjoying the surroundings. Felt right at home. The house was clean and very functional. Eddie was great to work with and I would recommend this to anyone wanting a home base for the Annapolis and surrounding areas.

We had a small family group stay at the Beach House in North East for Thanksgiving, and it was perfect in every way for our group. Plenty of room, fantastic location and water views, easy beach access, very well-equipped kitchen, warm and cozy living room area, and great communication from Alexis. We hope to return again soon!

The house was comfortable, clean and quiet. It was exactly what I was looking for to participate in a nearby competition. There were minor issues that the host addressed quickly and we got back to our vacation. Would stay here again.

Our family had a great time - the property was spacious and clean, location was beautiful, and we loved playing outdoors in the open space and getting out on the water. Hosts were very responsive and everything we might need/want was provided!

We had an incredible stay here! The house is so spacious and has so many places for people to gather. It was the perfect place for our little retreat. Hal was a great host and super responsive and kind. The views were also so beautiful. Can’t wait to return!