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.

Leisa’s home suited our needs to a T!! We were in town to attend a wedding at the London Town and Gardens, which was just a half mile away. The rehearsal dinner in downtown Annapolis was also a short distance away. Everything was fresh and clean, the beds were comfortable, and the showers were really great. The lack of seating in the main room wasn’t a problem for us as we didn’t spend much time there during the day. The area around the pool looked really comfortable and inviting for guests staying during the summer season! Would stay there again.

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

It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"

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 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

We stay at Marie's place every year for the Maryland 5 Star, and it's the perfect house for 3 couples. The kitchen is huge and well stocked, and each bedroom has its own bathroom. Marie is wonderful and communicative. We'll be back again next year, I'm sure!

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!

A beautiful home with gorgeous views of the bay. The host was super responsive and helpful.

Absolutely amazing house and location!! Our family had an incredible week spent enjoying the property & views, spending time watching the sunsets by the fire, and kayaking around the bay. It's a great spot to teach kids to paddle and our 7 and 9-year old both enjoyed learning on the still waters near the sandy beach. The property and house are both thoughtfully designed and have so many spots to relax, read, watch the birds, and take in the views - made it feel like there was never a reason to leave. We had an incredibly peaceful week and would love to visit again!!

Patrick was really helpful and communicated very well with us. He was very thoughtful and warmed the hot tub for us. He also let us stay till 230 past the regular checkout time without even us asking. The house was everything we could’ve asked for and the price was really cheap. The fields around it only added to the peacefulness. I may even come here again. It was really worth it. Thank you, Patrick.

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!

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.

Patrick and his co host Kelsey were great. The house was so fun and nicely done. So incredibly close to the docks and Main Street. Would stay there again in a heartbeat.

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.

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.

I have never stayed in a place that absolutely had everything we needed. I could have brought my clothes, shoes and makeup and basically been fine. The house was very clean. The furniture was comfortable and clean. The beds were comfortable. Town was 5 minutes away. We loved the shops and great restaurants. We would definitely recommend this house.