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“Can't Wait To Go Back”
Review of Widow's Walk Inn

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Widow's Walk Inn
Ranked #5 of 11 Chestertown B&B and Inns
Reviewed 1 August 2011

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 the middle of the bustle. The air conditioner was a little undersized for the size of the room, but most people would be fine using the overhead fan. Just turn the temp. lower than you expect. It was 100 degrees when we were there and we were comfortable. Widow's Walk is less pretentious than some but the price is right and Bob makes a great breakfast. Since about an hour and 45 min. from Baltimore, we decided it will be our getaway when we just need to relax.

  • Stayed: July 2011, travelled as a couple
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1  Thank eba5
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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Reviews (41)
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36 - 40 of 41 reviews

Reviewed 26 June 2011

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 stroll to town restaurants, and the waterfront. The property is kept absolutely immaculate inside and out, and is furnished with beautiful antiques. The Inn Keepers, Bob and Susan were extremely helpful prior to our trip with information on restaurants, and suggestions about the weekend. Breakfast each day was not only delicious but very entertaining. Bob's talent in the kitchen is obvious with the breakfasts that we shared each morning. We have never stayed at a B & B and felt so at home and felt so comfortable.

  • Stayed: May 2011, travelled as a couple
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Thank JeanM_11
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 19 June 2011

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 and welcoming feel. Whether we're spending quiet time reading or relaxing on the screen porch or find pleasant conversation in the living or dining rooms which, by the way, are appointed with many family furnishings and objects of the inns owners, Bob and Sue, we don't feel "funny" about using the common space as we have in some other bed and breakfasts. The rooms are ALWAYS clean and fresh as well as the bathrooms, and it seems all your need are thought of. The innkeeper is akways available, but doesn't hover. Breakfast is a treat, many times Bob uses fresh produce from local farms. We have found the rates are fair. If you are looking for a consistently comfortable, clean bed and breakfast in a absolutely lovely part of Maryland, this is the place!

Room Tip: Chhose the Susquehanna if you prefer privacy
See more room tips
  • Stayed: April 2011, travelled as a couple
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Thank FayeLeola_Pe
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
Reviewed 16 September 2009

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 on the "Widow's Walk Inn" and made reservations by phone. I spoke to Bob, the innkeeper, who said I could check in early on my way to Rock Hall instead of coming back in mid-day at the normal check-in time. This was a big convenience. Upon arrival Bob walked me through the rather large house and pointed out the amenities. I stayed in the Chesapeake Room which is large and tastefully furnished and has an en suite bathroom spacious for a Victorian-era B&B (there are some rooms that have shared facilitties). Returning after a day's worth of festivities, I had a great night's sleep in a very comfortable bed. Breakfast was perfect -- a fresh fruit cup, a variation of french toast, a choice of juice and outstanding coffee. There was no rush to leave and while checking out Bob and his wife Susan spoke about the history of the house and about the attractions in Chestertown. Parking is off-street and the inn is in a quiet neighborhood. The innkeepers are very cordial. I recommend this inn to others and would stay there again.

  • Stayed: August 2009, travelled solo
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4  Thank RMG4369
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC
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
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5  Thank Allan J
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
Amenities:
Hotel Style:
Ranked #5 of 11 B&Bs / Inns in Chestertown
Price Range: ₹ 1,946 - ₹ 8,757 (Based on Average Rates for a Standard Room)
Number of rooms: 6

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