Holiday 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 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 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!

This was our second time at Leone's beautiful spot on the Chester River and it did not disappoint! It's such a beautiful place and beautiful location -- we absolutely love it!! Thank you Leone!!!

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.

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.

the stay was wonderful. A very relaxing and peaceful place. Easy to locate and get into. reasurants and grocery stores are near by

This is a beautiful home in a serene setting. Although there was plenty of boat traffic it was I. The distance and not noisy at all. The home is furnished simply but there are many more amenities than most airbnbs including children’s equipment and toys! The host readily honored a special request! The pictures are not clear about the water access. It is not a beach, but a stairway. We still spent much time at the water’s edge, and sitting in those great Adirondack chairs!!

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

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

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.

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.

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.

This place was so peaceful. I really felt comfortable and relaxed. It’s a very beautiful area.

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.

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.😊