Vacation rentals with outdoor seating in Chestertown

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

This was my second time staying here with my family and dogs. We absolutely love the property and area! We enjoyed kayaking and are dogs enjoyed swimming and playing along the river. Ina was a great host and was responsive to our needs. It was a great experience and vacation!

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.

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!

Penny is an incredible host who really goes above and beyond! I greatly enjoyed my stay.

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.

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.

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.

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.

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.

Loved the location of this place peaceful and walkable to many restaurants. Was a little bummed with the pool hours but all and all would stay 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!

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.😊