House holiday rentals in Chestertown

We loved our stay at Molly's air B &B. there were lots of toys to use on the river. The water views from the house were fantastic. The house was clean and comfortable. We loved taking a dip in the pool. Great communication with the host.

The house was beautiful and clean. The lication was great! Too bad it rain during out stay so we couldn’t enjoy the pool and the backyard. Thank you!

Fabulous views of Chesapeake Bay, pool was great, deer everywhere, house was spacious with three living areas. Would definitely stay there again.

It was a great stay after a long day roaming around Washington DC and Maryland. The accommodation was clean and nicely decorated with very inspiring words of wisdom providing a cozy and comfortable retreat throughout our stay. Kelly has been very informative and detailed on the instructions to help us on a very smooth check in and check out process. The location was fantastic and quiet neighborhood. Overall, we had a wonderful time and would highly recommend this place to anyone looking for a memorable Airbnb experience!"

Wonderful property with lots of amenities!

The house is beautiful and worked well for our family. The host was very helpful and responded quickly to any questions we had. The grounds are lovely and very peaceful. Pictures don’t do this property justice.

Martha is a great host and her property is fantastic. There is so much space and several great amenities. My family loved the pool, pickleball court and fire pit. The house is spacious and everything was perfect for our stay. I just wish we were able to stay there longer! We will be back.

We got exactly what we planned for. We wanted a private pool to enjoy family time. The whole place was great. The only thing I didn’t care for were the bathrooms. They are a bit dated compared to the home. But other than that, it was very nice.

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

Katie’s house is beautiful and so very accommodating. We’ve stayed at several different Airbnb’s in town and this is our favorite one. The location is walkable to everything in town and it’s on a very nice part of the street. Highly recommend the house to anyone looking to stay in Chestertown. And Katie, the host, is so nice and helpful and most importantly very responsive!

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.

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 ⭐️⭐️⭐️⭐️⭐️

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.

We've been twice now and love Dorothy's place. The kids can run around outside and we can grill and relax. A great escape from the city. About 15 mins drive to groceries or whatever you need, 20 mins to Chestertown. Easy drives.

I cant say enough about how wonderful our stay was! Three generations of family members that were able to gather together for our sons graduation from college. Beautiful surroundings, gorgeous home, so relaxing with eveything we had going on. We will definitely be recommending as a place to stay and with an amazing host! Thank you Nicki!

Not only was our stay reasonably priced it was spacious and well equipped. Check out the Bed & Breakfast that is directly behind the house for a good bite to eat! A nice perk was the small community beach was in walking distance.

Our stay at this place was so amazing! It had something for everyone to do! I feel it was very kid-friendly with lots of sand toys, a kiddie pool and inside toy too. The kitchen was well- stocked! We used the brick oven one night and boiled crabs. Martha responded quickly to our questions. She made it very easy for us to get into the house. We most definitely would come back again!

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

We rented this property to attend a family wedding. It was perfect for me, my husband and our 4 adult children. The best word to describe is serene. Martha is an excellent host. So responsive and helpful. The photos are accurate but the feel is so much better. If we ever go back to Galena we would stay here again. Highly recommend.

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

The place was spotless and had all the amenities we needed for a 4 day stay. We enjoyed the water view and had a crab feast on the deck overlooking the water. It was a perfect Memorial Day weekend.

How can I write a review for this cottage other than it is the most beautiful peaceful place. The kindness and caring that Robert & Donna have shown, has made me love it here more! Staying in a remote cottage at what times feels like the edge of the world, I feel safe. Sunrises are out of this world, sunsets are wonderful too! Wildlife abounds, a lovely dock to walk out on and sit on the dock of the bay, or river as it were. Eastern Neck Island close by, easy to jump in your car, take in a sunset, go check out swans, or venture to a butterfly garden. You may even get a boat ride from Robert! They few times I have "broke the cottage", they have come to my rescue promptly. You could not ask for a more wonderful place with more wonderful hosts, and you will sleep really well! Beautiful place with everything and more your heart could desire! I hate to leave this place, but whenever anyone I know needs a lovely place to stay I will recommend it. Who knows, I will return!