Vacation rentals with outdoor seating in Chestertown

The home was lovely, right on the river, and felt....homey. It was the kind of place I would have if I had a home on the river. There were friendly neighbors who gave us some advice on what to do/not to do in the area and we had a lovely time. This might just be an annual trip for me and my extended family.

We loved this stay! The lite house was very nice and renovated, while still maintaining original structure. The porches all around were great and the view from the master bedroom was stunning. Easy walk to small private beach. Town is about a 10 minute drive. We dined at Woodys and the Wellwood and they were both tasty!

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.

I booked this stay for a work project. After a busy day, it's a peaceful place to unwind in the evenings. The host is always quick to respond and the place has everything I could need.

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.

Laurie’s place was just liked it is described. It’s located in a beautiful area and walkable to all the attractions in Annapolis Maryland. I would recommend it and I would stay there again if ever back in Annapolis! Thanks for wonderful stay!

Tim’s house was perfect for our group of 4 adults and 4 kids. It’s very cute, clean, and spacious. His level of hospitality did not go unnoticed, he seemed to of thought of everything. The kitchen was well equipped for cooking if you choose to do that. We would definitely stay here again!

Our stay at Justin’s Hot Tub Haven in Annapolis, was exactly that…a haven with a much enjoyed hot tub! Justin was exceedingly responsive, proactive, and flexible. The home is very well appointed with all the necessities, plus all the thoughtful touches like umbrellas, a doggie waste station, and bath robes to name a few. Our children loved the downstairs space (and secretly the adults were thrilled they had it too), and it felt to them like they had their own little apartment. The backyard felt like a small resort. We loved the quick walk to shops and the our boys loved the nearby basketball courts and baseball fields. We highly recommend this home and will stay here again!

only stayed for one night but i was very comfortable. the toiletries and snacks were an appreciated added bonus.

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

I loved staying at Thomas’s place! It’s ideally located in Mount Vernon with lots to do around the area including spots to eat and cute bars. It’s also a somewhat short walk to the train station which is convenient. The apartment is special…very quirky in a wonderful way. I had everything I needed for a comfy stay. The kitchen is fully equipped with pretty much anything you need. The bed was extremely comfortable - that’s rare to find for me! The host is super responsive and kind. All said, this is a 5/5 for everything and I’ll definitely stay again when I’m in town.

Heather's place was as described. Clean and neatly organised. The linens and towels were very clean. The facilities available were adequate. The kitchen is not a full kitchen but has enough for heating. We had left some medicines behind and Heather and her team spotted it, and communicated the same to us. In addition, they took the trouble to drop it off at the local FedEx office.

The location is ideal! It’s a quiet , safe and very walkable neighborhood. The bed is very comfortable and the apartment is well equipped for anything you might need. Very close to the waterfront, great restaurants and of course Camden Fields. We loved staying here.

Absolutely amazing! The place had so much to do whether it was outside or in! Swimming in the pool, hot tub, kayaking and/or paddle boarding on the lake, giant yard games. Inside had a pool table, wide variety of board games, and many streaming services. Brenda was extremely friendly and helpful in many way. She had a binder full of local places for food and things to do! She truly showed us the best of Maryland.

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.

Perfect location for exploring Annapolis attractions via walking including Naval Academy and downtown. A bonus for me, all areas were wheelchair accessible (except balcony). Very clean and well maintained! Bed was super comfy!

Wonderful stay in Chestertown! Hosts go out of their way to may the experience pleasurable. Would 100% stay here again!

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.

Great host, great location. Walkable to great restaurants as right over the bridge from Main Street Annapolis. The pool is literally right in front of the apartment overlooking the water and the boats going by. The place is not huge but location, location, location.

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!

Sean’s unit is an amazing option for those who love a great place to relax with an amazing view. Sean is a great host and very communicative.

This was a beautiful, and comfortable apartment to stay in. David was an incredible host. This was our first time in Annapolis, which is a beautiful town with a lot to do, and plenty of great places to eat. The location of the apartment was perfect, and was in short walking distance of pretty much everything. If you are looking to stay in Annapolis, this is the spot. Really comfortable, and has an awesome deck to sit outside and enjoy a beverage on. Thanks David!

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.😊