House holiday rentals in Chestertown

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!

Staying here made our family wedding stay away from home, a very memorable and fun weekend for the whole family. Muvh better than being stuck in a hotel with lots of kids!!

This was a great place for our family of 13 to stay during the weekend of our niece's wedding in Baltimore. The home has plenty of large common areas, dining space, and super comfortable beds - even the queen-size bunk beds on the lower level had high-end mattresses. The kitchen is well-equipped. We had 4 additional family members drop in for dinner on our last night there, and it was no problem preparing food for, and serving, 17 people. Everyone was happy with this choice for our accommodations.

Great home best Air BNB we have stayed in. My family of five and our dog had a great time, plenty of room, partial sunset from the hot tub. Beautiful sunsets right up the road. The community has a beach area and piers for fishing crabbing etc... Lonnie was really great she got right back to us with any questions or needs. Annapolis, Naval Academy were really close, lots of great places to eat, marina's everywhere. DC and Baltimore are a 1/2 hour 45 minutes away. Everyone was very friendly being from NY it took a bit to get used to waving at strangers. Went in April the Hot Tub was awesome have to come back when the pool is open. Great place for a family vacation.

I can’t say enough wonderful things about Melissa’s place. As soon as you walk in, you feel right at home. She has thought of every possible thing you could need while there. The views were absolutely magnificent and while the beach area is available to the public, it felt super private. My daughters and I plan to come here every year. I had to peel them away from the bay. Melissa, thank you for accommodating us. This was a weekend my girls and I desperate needed and your home was the perfect place to have peace and intentional quality time. Thank you so much!!

We stayed at the house for a family wedding. We had a total of 7 people staying in the house and there was plenty of room and beds for everyone. The house has everything you could need! The backyard is beautiful with a view of the water and access to the water. The host gave clear instructions and made it easy to get into the house! I would definitely stay in the house again and recommend to anyone in the area. The area is beautiful and we found some great seafood restaurants!

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

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!!

Danielle was always responsive to anything I needed help with. The home was perfect for our family and the backyard was awesome for the kids to kick around a soccer ball! Driveway was a little challenging for me, but otherwise everything was perfect!

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!

We loved our stay at Tracey‘s place! The animals close to the backyard we’re so fun to visit! The kids could go out and see them while I was in the kitchen and I could keep my eye on them which was great! Even when an issue came up with the house, Tracey was very gracious and reasonable!

- 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!

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.

Home was spacious and very clean, nice layout with one bedroom downstairs and 3 bedrooms upstairs, full bathrooms on both floors.

We had a very comfortable stay. The house was spacious, clean, and convenient to BWI, grocery stores, and I-97. It was a really good value in an expensive area. We want to stay here when we’re back in the area.

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.