House holiday rentals in Chestertown

We had a great time. The view is one of the best we have stayed at. The hosts have thought of almost everything you could need or want to do. Our kids wanted to come back just to do more of the activities. The interior is obviously dated but it is thoughtful, functional, and clean. We felt cozy and at home! We will be back!

It was amazing.The pool is so fun.We had bad weather but we were still a little inside.The location is quiet and beautiful. We will come back for sure. Thank you

Place was great and large enough to accommodate 2 families (9 total people). We were excited to have a place with a pool but didn’t end up using it because it was a little chilly. Neighborhood was quiet and early morning walks were pleasant. Beds were comfortable too.

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

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.

Perfect for a family getaway and retreat. Love how child friendly their home was as well!

we were looking for something out of the city, private for three businessmen to do some planning for the remainder of the year in beginning of 2025. I found Eli's place exactly as described, sitting out on the edge of the water and Adirondack chair was peaceful and exactly what we needed. It's a short drive in and out of the city so we we were in downtown for a little sightseeing and then made the short trip back to solitude. The house is exactly as described, while we didn't use the game room we did look at it. everything was clean, exactly like the pictures and highly recommended.

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.

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!

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

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!!!

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.

Such a lovely little cottage in a sweet little town on the bay. Peaceful, clean, and well equipped. Highly recommend staying here and enjoying the screened in porch where all you can hear are the owls and the crickets. Michele gave great instructions for parking/arrival/etc. We hope to come back!

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.

Nicki was an exceptional host—responsive, thoughtful, and truly dedicated to providing a wonderful experience. The home was absolutely stunning, equipped with everything we needed, and her attention to detail was impressive. She truly thought of everything, making our family trip seamless and memorable. The property was in pristine condition—immaculately clean, set in a peaceful and quiet location with breathtaking views. I honestly can't say enough great things about this home! As a Realtor, I will be recommending it to all my clients, family, and friends. We can't wait to rebook our stay there again soon!

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!

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.

This was such a peaceful and beautiful getaway. The house was so charming and immaculate. That goes for interior and the exterior. We celebrated Father’s Day weekend here and our husbands had a blast fishing the pier and our littles walking to the beach. The rain head shower head and the heated bathroom floor was to die for, and enjoying a book on all the wonderful porches and beautifully kept backyard! We hope to visit again soon! Thank you so much.

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!