Vacation rentals with a washer and dryer in Chestertown

As a repeat guest, Sean consistently provides a 5-star experience. Sean’s communication is friendly and responsive and the home is clean, comfortable, and in a great location. Even when I had a question in the middle of the night (which was already answered in the digital manual which I missed!), Sean was kind and understanding enough to immediately respond without judgment or matter-of-factness. If you’re looking for quality service, this is it. A gem!

It's a much better accommodation than what you see in the photos- I don't regret staying for a long time-

John was nice and responsive when I had questions. Also the apartment looked nice

We booked Erma's place for our birdwatching adventure. I had the master bedroom, which was large with comfy bed. My sister slept well on the futon in the second bedroom. Although she sometimes heard people walking around upstairs, their schedules aligned with ours, early to bed and early to rise. Then they were off to work and we went birding at the many wildlife refuges available. We cooked in the small kitchen, with plentiful supplies and condiments, and picked up groceries at Bylers and other nearby stores. The living room was large and comfortable. The large bathroom was conveniently off the living room. Since it was a little chilly with the ac on upstairs, we simply followed the instructions to close the vent and we were fine. Parking was convenient, and we sometimes hung out in the peaceful backyard, occasionally walking over to see the chickens. Erma responded promptly to any questions that I texted.

Had a great time! Kathy and wayne was very helpful on suggesting restaurants and things to do. We loved the dock and fishing! They made sure we was right at home when we interacted with. This was a good central place to all we wanted to see, we went to Hersey Pa. Washington dc., The beach(bay) area, Baltimore harbor.

Cute and cozy! I felt right at home. Jordan and Danny are very nice folks, the apartment is very well appointed. There is a dock on the property that I should have spent more time on. The bed was a dream to sleep in and I literally overslept my alarm the first day. You will definitely need a car to get around but the apartment is a 3min drive to Safeway, Walgreens, Starbucks, etc. The neighborhood has a homey feel and the apartment has a homey feel which was my jam. My dog had a little accident but I got some carpet cleaner and let Jordan know and she was very understanding. I would definitely stay here again if I am visiting Kent Island.

Anne’s place was great for my week long stay in Baltimore. It was about 17 minutes from JHU, less than 15 minutes from the Harbor and National Aquarium, close to Baltimore local favorites, and directly across from a park. Anne was responsive to all my concerns and needs. The apartment was clean and had an abundance of extra towels and sheets for our use. The only comment I have is about the TV and Wifi which were both slow and lagged when doing work. Everything else was perfect and I would definitely stay there again.

We love staying here. The bed was super comfortable. It was a walking distance from so much to do. Jeremy was super helpful and went above and beyond. We just really loved staying here.

It was a very clean and the location is ideal for any downtown activity! The host was very accommodating!

Great location. Caroline was amazing. Look forward to renting again next year!!

We had a short but nice stay here! We really appreciated the quick responses and thorough explanations of everything. We also appreciated the cookies and couple of waters that we so desperately needed after such a long trip! The place itself is just how it looks in pics and isn’t too far away from the downtown area ☺️

We stayed for the weekend when our son had a baseball tournament. One of teammates came with us and this was perfect for everyone to have their own room and space to spread out. The house was neat and clean and we felt right at home this weekend. Would definitely consider staying here again if we’re ever back in the area.

Beautiful location and the bikes, kayaks and fire pit all added fun and relaxation to our stay! Close enough to Chestertown to enjoy the farmers’ market and shopping and far enough out to be a peaceful retreat.

Just a wonderful location. Very private and the property is beautiful. The house was well-equipped; it included a couple of kayaks that we used on the Choptank River, where we saw ospreys, eagles, and even a beaver. The beds were comfortable and the decor and other items in the house were very interesting. We likely will be back some time.

This house was perfect for our stay in MD. Our family of six was very comfortable here and our kids loved the pool and spa. The house is clean, cute and very cozy. Tanya was very quick to respond and great to work with!

Lovely house in a beautiful and peaceful setting. Well equipped kitchen, bathroom and cozy, comfortable bedding and beds! I recommend Diana’s place for a peaceful and relaxing stay.

Ellen’s condo was absolutely perfect for Commissioning Week. The location couldn’t have been better—within walking distance to fantastic restaurants, the Naval Academy, and Graduation at the Navy-Marine Corps Memorial Stadium. The coffee shop downstairs was a delightful bonus, and the underground parking was a major perk. Ellen provided clear and detailed instructions about the condo and guest expectations, making everything easy to understand and stress-free. The condo itself is beautifully and tastefully furnished, with all the essentials thoughtfully provided. The in-unit washer and dryer were a huge convenience. The bathroom was spacious and well-appointed, complete with shampoo, conditioner, and body wash. What I appreciated most was how quiet and peaceful the condo was—it offered a true retreat. The private patio was perfect for enjoying a morning coffee or an afternoon cocktail. I would absolutely stay here again.

We had a great time once again staying here. It is just steps from the main gate of USNA and the downtown activities and restaurants. Caite was also responsive and very flexible with us and our needs.

We were in town for Maryland Deathfest. The place was located within walking distance of everything we needed.

If you’re lucky enough to find Mandi’s place available during your preferred dates, don’t wait and just book it. This spot is adorable, comfy, across the green space from restaurants and shops, and walking distance to the water as well. Also be sure to make your booking for a salt water float at Mandi’s spa on the ground floor. I booked an hr for Mother’s Day and I felt like a leaf floating on the top of a pond in a tranquil cave. Even more relaxing than a massage in my book. I’m already hoping to come back as soon as I can. Thanks Mandi for being such a lovely person on top of all that!

Jordan and his place were both amazing. As avid gamers ourselves, this was a walk down memory lane. All linens and kitchen ware were available. You can cast your apps on the Google TVs, which is a huge bonus. There are tons of food places within 5 minutes walking distance and we were able to to walk to the CFG Bank Arena for a show with in 15-20 min. Saves on parking or Uber/Lyft costs. Jordan is extremely responsive and even recommended local eats. They were delicious. Thanm you so much, Jordan. It was a delight having you as a host.

Gerald's place was perfect for our 4-day girls' trip. The three of us stayed and had such a great time. Everything went smoothly. The home is beautifully decorated with high end furnishings, comfortable beds, great WiFi, and every comfort of home. It looks just like the pictures. Street parking was very convenient so we never used the dedicated parking lot. The neighborhood was pretty quiet and felt safe enough for us, 3 women to walk around. Our host checked in with us to make sure we had everything we needed but honestly, we didn’t need a thing, they had everything anyone could want for a pleasant and comfortable stay. We are happy we chose this place and would not hesitate to stay here again.

My family & I booked for three nights. Thought it was a beautiful and private little area, and just a couple steps away from the beach and a pool. Very quiet and away from noise which was a plus. The house itself was lovely and mostly clean. There were board games available and my kids had a fun time playing with them. We enjoyed barbecuing using the grill provided on the balcony which was nice as well. A plenty of towels and anything you need in the kitchen! Other than a full trash bag left over in the kitchen, finding some clothing items from other guests (I’m assuming) in drawers, and the keurig having what looked like mold inside. Pretty small things when looking at the big picture though. Will most likely come again & we enjoyed our stay!

We had a great stay at Casey’s Moon Base Airbnb. The condo was exactly as described . The neighborhood was friendly and safe. There are several restaurants and shops just a quick walk away. We were able to walk to a Johns Hopkins graduation through a lovely park. Casey was friendly and responded quickly.😊