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Widow's Walk Inn
Ranked #6 of 11 Chestertown B&B and Inns
Reviewed 30 January 2009

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 antiques and semi-antiques. Perhaps too much so, as I felt everything had been arranged "just so" and that it would be bad form to move anything. Certainly a family with children would have to be on tiptoe here.

That said, the room and bath were spacious, comfortable and spotless -- and the price was perfect.

Innkeeper Bob had hot coffee going not long after dawn, and made me a breakfast that lacked for nothing.

The main part of the town is just five minutes walk away -- beautiful town -- and dinner at the Blue Heron is not to be missed.

  • Stayed: June 2008, travelled on business
    • Value
    • Location
    • Check-in / front desk
    • Rooms
    • Cleanliness
5  Thank Allan J
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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40 - 41 of 41 reviews

Reviewed 20 June 2006

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 Victorian home was the dining guidance provided by Bob and Sue. Lunch at the Old Mill Bakery was wonderful - generous portions of all menu items - fantastic sandwiches and excellent soups, all made with top-of-the-line ingredients.

Dinner at the Blue Heron was even better - thick tenderloins that cut like butter, excellent fish and immensely wonderful crab and shellfish! A rare find in a major metropolitan area, quite unanticipated in this sleepy little town.

Exploring one day, we found a wonderful place in Chesapeake City (about an hour away) called the Bayard House. We lunched there, outside, on the canal, under an awning. This establishment had a very pleasant staff and the food was well prepared and excellent in all regards.

All told, a wonderful place for a quiet day or two of relaxation.

  • Stayed: June 2006
    • Value
    • Rooms
    • Cleanliness
    • Service
5  Thank Charlotte_Transplant
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Additional Information about Widow's Walk Inn

Address: 402 High St., Chestertown, MD 21620-1312
Region: United States > Maryland > Chestertown
Hotel Style:
Ranked #6 of 11 B&Bs / Inns in Chestertown
Price Range: £22 - £101 (Based on Average Rates for a Standard Room)
Number of rooms: 6

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