Just returned from a week-end in Chestertown and stayed at the Widow's Walk. While we enjoyed our time in Chestertown and Rock Hall, our stay at this Bed and Breakfast made the difference. It really felt like home away from home. The place is immaculate, inside and outside. The interior design/decor is fabulous, yet cozy and inviting. Our room was... More

Widow's Walk Inn in Chestertown, MD, is a wonderful, relaxing B & B with very hospitable hosts.The best part of all was the Saturday morning breakfast of baked Blueberry French Toast which is to die for. You must request it! I am a breakfast lover and this is by far one of the best breakfast dishes I've ever had. Enjoy... More

We've been staying with Bob and Sue for the last four years. The Widows Walk is beautiful inside and out with huge, comfortable rooms. I get up early to chat with Bob every morning and catch up on Chestertown news. Breakfast is wonderful and, Bob will kill me, but ask for the' blueberry puffs - incredible. More

Widow's Walk was not our first choice but will be from now on. A great Victorian house and a wonderful host in Bob. Just ignore his teasing! We looked online at others which were not available midweek in the summer so ended up at Widow's Walk and are so glad. It was in walking distancce of everything but not in... More

My husband and I spent Memorial Day weekend at the Widow's Walk Inn in Chestertown, MD and have already been talking about returning. We have stayed in many B & B's and Inn's and this is by far one of our favorites. The Inn itself is a beautiful Victorian in an excellant location on High Street which is a quick... More

My husband and I have been staying at the Widow's Walk since 2005. I chose it that year from any number of inns in the area because of its proximity to the shops in Chestertiown, you literally walk out the door and onto the historic streets. We continue to return year after year because the Widow's Walk, has a comfortable... More

I made up my mind to attend the Pirates and Wenches Fantasy Festival in nearby (13 miles away) Rock Hall, MD. Unfortunately, I decided late and could not find a room for a Saturday night close-in Rock Hall. Since I had to pass through Chestertown, MD to get to my destination, I looked at B&B's and hotels there. I decided... More

I arrived on a summer weekday & was the only guest, which I gathered was quite common during the week. As the innkeepers live in the carriage house, I had the house to myself... and saw (and heard) the innkeepers only at check-in, and then breakfast 15 hours later. The house is large, tastefully -- even expensively -- furnished with... More

We stayed two nights in this inn and found our hosts, Bob and Sue, to be extremely gracious and helpful. The rooms are spacious, clean and very comfortable. Breakfasts provided were delicious and the coffee was excellent. The public rooms of the inn were comfortable and the atmosphere was quiet and relaxed. Even better than the ambiance of the old... More