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“Great Time, We Will be Back” 5 of 5 stars
Review of Widow's Walk Inn

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Widow's Walk Inn
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402 High St., Chestertown, MD 21620   |  
Hotel amenities
Ranked #4 of 12 Chestertown B&B and Inns
Pittston, Pennsylvania
2 reviews
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 1 helpful vote
“Great Time, We Will be Back”
5 of 5 stars Reviewed June 26, 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, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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28 reviews from our community

Traveler rating
    24
    3
    0
    1
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Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    5 of 5 stars
  • Rooms
    5 of 5 stars
  • Service
    5 of 5 stars
  • Value
    4.5 of 5 stars
  • Cleanliness
    5 of 5 stars
Traveler tips help you choose the right room.   Room tips (8)
Date | Rating
  • English first
  • Any
English first
Leola, Pe
1 review
5 of 5 stars Reviewed June 19, 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
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  • Stayed April 2011, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 4 of 5 stars Service
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Virginia
Senior Contributor
25 reviews 25 reviews
4 hotel reviews
Reviews in 11 cities Reviews in 11 cities
16 helpful votes 16 helpful votes
5 of 5 stars Reviewed September 16, 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, traveled solo
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 3
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Greenville, South Carolina
Senior Contributor
27 reviews 27 reviews
17 hotel reviews
Reviews in 22 cities Reviews in 22 cities
28 helpful votes 28 helpful votes
4 of 5 stars Reviewed January 30, 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, traveled on business
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Check in / front desk
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
Was this review helpful? Yes 4
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Charlotte, North Carolina
Senior Contributor
48 reviews 48 reviews
6 hotel reviews
Reviews in 18 cities Reviews in 18 cities
25 helpful votes 25 helpful votes
5 of 5 stars Reviewed June 20, 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
    • 5 of 5 stars Value
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 5
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
Location: United States > Maryland > Chestertown
Amenities:
Hotel Style:
Ranked #4 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $
Number of rooms: 6

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