Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

Words aren't enough....a picture is worth a thousand words. The adages are true, until Chessie Cottage. You have to BE there to believe it. We have been renting houses up and down the east coast for over 30 years and not by any choice of our own, have sort of become vrbo snobs! Never has a place tickled all of our fancies until this one. There is quite honestly nothing the hosts haven't thought of for one's comfort and artistic pleasure, and neither is there a more peaceful spot on the coast to while away a day, a week, or whatever your heart desires. We have found our unicorn and struggled to pack up and leave. Thank you for making our stay picture perfect for us and the fur baby.

We thoroughly enjoyed our stay at Chessie Cottage, from booking, through checking out. The owners greeted us and gave us a tour….we have rented homes on the Chesapeake for almost 20 years and this was the best greeting we have ever had; they were warm, welcoming and helpful. The home is stunning, completely stocked, and comfortable. The view…..amazing! The host, Janet, also went out of her way to make our stay wonderful. We highly recommend this home and the host. We will be back! Elizabeth, Kevin, and our dog Rocky.

Amazing cottage — beautiful views, very comfortable rooms with great attention to detail, amazing kitchen for those who like to cook. Bonus was that it’s pet-friendly. A great place to relax, retreat, feel cozy in the fall weather.

Perfect location. Had wedding nearby. Stayed with 2 friends. We each had own bedroom or bed as well own bathroom. Couldn't have been better. Beautiful long weekend, sat outside and watched the sun set. Saw a Great Blue Heron and Eagle Hawk in the back yard. Well equipped kitchen , owner thought of everything. Visited Annapolis, about a thirty minute drive. Also visited a nice walking trail which was about a10 minute drive from house. Definitely would recommend.

This property was beyond prepared for our stay including eggs and bacon as well as many other snack items. It beautifully decorated and very comfortable.The out door seating areas on the porch and lawn are great for viewing ships on The Chesapeake. 10 minutes from anywhere you need to be. Little touches like labels helping you find whatever you need and navigating the wall switches for lights and ceiling fans.We loved our mornings with coffee on the porch and evenings with cocktails.So much more could be said, but this is a fantastic property and it made our stay far better than if we had used the hotel.

Checking in was easy and the manager, Janet, met us and went over everything. There was a detailed notebook explaining how to work everything and house rules. The open kitchen was beautiful and stocked with everything we could possibly need. In the frige, there were eggs, butter, and other snacks. A welcome basket of chocolates was also there. The appliances were all brand new.

We absolutely loved our stay at this cottage! It had everything you could possibly think of - so many thoughtful extras and incredible attention to detail. The hosts truly anticipated every need. The view from the back porch was stunning and the perfect spot to start each morning with a cup of coffee or tea. We didn’t bring our dog this time, but the space was so pet-friendly that we’ll definitely bring him along next time. Highly recommend!

This was our 3rd time staying at the Chessie Cottage and it was another great experience. We love everything with the home and enjoy every minute watching the ships pass by and the amazing sunsets. Can’t wait for our next visit!

My husband and I and our little pup Bree stayed for a long weekend - and from start to finish everything about this cottage was just amazing. EVERY amenity is there and thoughtfully provided - you want coffee? It's there with little mug hats to keep it warm as you sit and watch the boats go by - you feel a chill? There’s cozy blankets for the beds AND pup - even beds, bones and toys for Bree. If you think of something you need - trust me they already thought of it and it's there for you to use. And now - the VIEWS!!! I can't even describe how beautiful - rating how beautiful the sunsets each night was our pastime. And the house itself is wonderful - so warm and inviting - modern but uniquely eclectic and cozy - and when you're inside it feels much larger because of the high ceilings and massive windows that give views throughout the house end to end. This is where you want to be on Kent Island - I'll never go anywhere else.

We had an amazing weekend. Great location right on the Chesapeake Bay with amazing sunset views. A very tranquil setting. Loved sitting in Adirondack chairs watching the birds and boats passing by. The house was beautiful inside and out and had every possible amenity you can think of. Hope to be back for another visit soon.