House vacation 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!

Rick was very supportive and his communication was superb. Great host with a beautiful cozy home. 5 star all across the board.

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.

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!

The red point lighthouse was all you can dream of for a beachside vacation and more! The house feels even bigger than the pictures make it seem and everything was clean. The beach isn’t private but it’s rarely ever crowded since it’s reserved for residents of the area. You’re not within walking distance of restaurants or stores but we didn’t think that was a problem at all; we stocked up on our way down and even passed a house selling eggs and homemade cinnamon buns which we bought for breakfast one day. I would highly recommend staying here and hope to be back!

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 a great host and responded quickly to different inquiries prior and during my stay. The home was beautiful and was perfect for a fun and relaxing weekend away which was exactly what I was looking for. Would come back again

An Unforgettable Couples Getaway Thank you so much for allowing us to host our couples gathering at your beautiful property. The home was not only stunning and well-appointed, but it also created the perfect atmosphere for a weekend filled with connection, laughter, and unforgettable memories. The care and attention to detail in preparing the space did not go unnoticed. From the beach towels by the hot tub to the extra bedding that came in handy (especially since I forgot to mention my feather allergy!), everything was thoughtfully stocked and readily accessible. Our group felt immediately at home. Finding a property that can comfortably and effortlessly accommodate a group like ours is rare—but yours exceeded every expectation. We’re incredibly grateful for your warm hospitality and would gladly recommend your home to anyone looking for a cozy, welcoming place to stay. We hope to return again in the future!

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!

The place was perfect and we loved watching the sunrise over the bay every morning. Nice quiet neighborhood and great fenced in backyard for the dogs. The house was as described and looks like the photos. The host was very responsive and helpful! Would definitely recommend this home to anyone looking to come to the Annapolis area.

- 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.

Esther’s place was clean and nicely decorated. She responded quickly when we had questions. Very nice and friendly host, would definitely recommend and stay again.

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!

Absolutely beautiful place, very spacious, and very clean! This was the best Airbnb I have ever stayed in - I can’t recommend enough! Five bedrooms and 3 bathrooms was the perfect size for our group of nine. All of the furniture was so nice and new. The location is perfect on a quiet street but walkable to downtown Annapolis. We were able to park multiple cars in the driveway and there’s a parking garage just a short walk down the road if needed. Danielle was an excellent host, very responsive, provided clear check in instructions, and she checked in part way through our stay to make sure everything was going well. I would love to stay here again!

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.