Vacation rentals with a patio in Chestertown

It exceeded my expectations based off of the pictures I had saw. Super easy check in and they even left a handwritten card and some snacks for us. Thanks Josiah for the welcoming touch!

Great weekend stay in Baltimore. Would book again! The place was clean, easy to find, and stocked with everything you need. Parking was tough but overall location was great with lots of walkable places nearby and a quick uber or car ride to other attractions in the area.

WOW! My family and I cannot say enough great things about Jeanne's Airbnb already planning our next trip! First off the property is an oasis in itself with a massive deck overlooking the inlets of Chesapeake Bay we woke up every morning to a beautiful blue heron eating breakfast right on the dock, having access to kayaks to explore the waterways was a huge bonus too, not to mention the gazebo with a fire pit we enjoyed roasting marshmallows and talking about the days adventures as a family. The inside of the Airbnb is extremely well thought out with every amenitie that anyone could ever ask for, from a well stocked and equiped kitchen, to the king size master bed with luxurious soft linenes, to the heated fan that greets you after a perfect water pressure shower. Seriously, this place is perfect a hidden gem for sure with easy access to so many wonderful Maryland attractions. Can't say enough great things about this experience and Airbnb can't wait to return!

This place was really great! It looked like the pictures and was exactly as described. Where it excelled was going past that. The small details that we didn't expect. Kim really thought of everything and it felt like going to a friend's house that really pulled out all the stops. She set bikes out for us to use. There were beach chairs, a cooler backpack, picnic blanket all available for us to use. There was a snack basket for us. A gallon of water and water bottles in the fridge. The kitchen was fully stocked with anything we could ever need. The bathroom had extra toothbrushes and other things we may have forgotten. The area was very nice and the sunsets at the beach were beautiful!! If you read this far, stop, just book it already!

The apartment was located near everything we wanted to do at the inner harbor and beyond. The space was well appointed with everything we needed. It was very clean and extremely cozy. The bed was so comfortable and the hosts were very responsive and friendly to any questions we had. Thank you, Matthew and Elaine!!

It exactly as advertised. Nice and quiet, close to downtown, was very clean and private. Would definitely recommend to anyone!

Michael and Melodie are great hosts! Friendly, proactive and immediately responsive to whatever minor needs we had. The place is new and squeaky clean, with all the amenities we needed for our short stays. The entrance is tucked off to the side, so it truly does feel private. But the icing on the cake is having a fire at sunset and looking out over Middle River. We loved it so much we booked the place again and had a second one.

What a gem! This beautifully renovated home, located in the heart of Chestertown, exceeded all our expectations. It was hands down the cleanest Airbnb I’ve ever stayed in—so spotless, I wondered if we were the first guests. The location couldn’t be better: right on the main street, walking distance to restaurants, shops, and with the farmers market just outside the front door. Evergrain Bread Company, a fantastic bakery, was right across the street. The home is adorable and the layout was perfect for my mother, who has mobility challenges. The beds were also incredibly comfortable. Katie was a wonderful host and left us thoughtful touches—wine, an amazing cheese tray, sodas, and snacks. I loved starting my mornings on the front porch with a cup of coffee. This was a last-minute getaway with my mom, and we loved it so much we’re already dreaming of our next visit. Highly recommend!

We had a great time in Rock Hall, Curtis was an excellent host!

Great location away from city living , beautiful home away from home , & surrounded by total quietness .

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!

It was perfect for what we were looking for. Location was convenient to Annapolis, but in a quiet area and right on the water. It was a peaceful and restful weekend!

great host, location, and space! i stayed here for my graduation and it was the perfect space- in pristine condition and so homey (solid set of amenities). i loved the master bed which connects to the rooftop and has it own bath. kenneth was consistently fast to reply and very helpful, and friendly! location was about a 30min drive from homewood field (JHU), but many restaurants and promenade by the water close by (walkable). would definitely recommend and stay again :) tysm kenneth!!!

Cindy's place was very relaxing with beautiful surroundings between farmland and forests.

This house was in a beautiful location. Everything was clean and comfortable, thoroughly enjoyed our stay. You cannot beat the views from the main level. Katie was communicative and we were even able to get an early check in!

We had an amazing weekend and Gregory’s home was perfect. So clean and well equipped. Gregory thought of everything!! Highly recommend ⭐️⭐️⭐️⭐️⭐️

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!

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.

This was an awesome stay! If you have infants their place is a must as it is easily baby proofed and has so many accessible items!

Scott was a wonderful host! Lovely place for two people or single person. Everything was super clean and orderly. Easy walk to Annapolis.

Alexander’s place is great. Peaceful, clean, and in a walkable neighborhood. Very responsive host. We enjoyed our stay.

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!

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!

What a perfect weekend get away. The place was perfect. Extremely comfortable beds, lots of pillows and two deck areas outside. We cooked outside 2 nights - and loved seeing the bay from the deck. We used the nearby tennis and basketball courts, and spent the days visiting wineries and neighboring towns, and driving through the countryside. Groceries and restaurants require some planning and some driving. Loved our stay!