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“Perfect for Business or Leisure” 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
Palm Springs, California
1 review
“Perfect for Business or Leisure”
5 of 5 stars Reviewed June 11, 2014

I have stayed here twice while on business in the area. The location is great, close to everything Chestertown has to offer. The rooms are clean and the entire inn is in great condition. It is very quiet and I slept better here than any traditional hotel. Bob prepares a delicious breakfast, something different each day. He is a wealth of knowledge about the area and can recommend the best restaurants in town.

Stayed May 2014, traveled on business
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28 reviews from our community

Traveler rating
    24
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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
Whippany, New Jersey
2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed June 7, 2014

My husband & I had a lovely time staying at the Widow's Walk Inn even though it was much too short as we were in Chestertown only for one night. Our first floor room with the en suite bathroom was charming in it's decorations. Our host, Bob, prepared us a delicious breakfast, honoring our vegetarian request. The Inn is conveniently located close to the various highlights, including Washington College, of this small town (and proudly so according to Bob) on Maryland's Eastern Shore. We will definitely be staying here when our travels bring us to this area. We hope we get to come back soon.

  • Stayed June 2014, traveled on business
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Lexington Park, Maryland
Senior Reviewer
6 reviews 6 reviews
Reviews in 2 cities Reviews in 2 cities
5 of 5 stars Reviewed May 27, 2014

We've stayed here several times. The location is great, the house is beautiful and the breakfast is wonderful. Bob has lots of suggestions for local explorations and clearly is proud of Chestertown and the Eastern Shore.

  • Stayed May 2014, traveled as a couple
    • 4 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Frederick, Maryland
Senior Reviewer
8 reviews 8 reviews
5 hotel reviews
Reviews in 7 cities Reviews in 7 cities
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed May 2, 2014

My sisters and I recently rented the entire bed and breakfast for a weekend trip to my daugther's art show and thoroughly enjoyed our stay at this beautiful bed and breakfast. Bob goes out of his way to make you feel welcome, made us a wonderful breakfast and talked with us about interesting facts of Chestertown. The rooms are beautifully decorated, beds very comfortable and the place is super clean. Also, what we loved was the location...some of us strolled down to the second hand store, others the farmer's market, while some walked around to take photos. Also, this place is very reasonable in price compared to others I have stayed in.

  • Stayed April 2014, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
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Hagerstown, Maryland
2 reviews
Reviews in 2 cities Reviews in 2 cities
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 21, 2014

My family took a trip to Chestertown to attend a Special Event. We stayed at the most wonderful B & B, Widow's Walk Inn. For some us this was a 1st time at a B & B. It certainly will not be the last time at Widow's Walk Inn. The Inn is within walking distance to all of downtown. Bob, one of the owners prepared a delicious breakfast for us & served it in the beautiful formal dining room. I highly recommend staying at Widow's Walk Inn. Yes, Bob if I had the money I would gladly buy it from you but I know in your heart you would miss the people. It is obvious you are a people person! It was a pleasure to meet your lovely wife Sue also.

Room Tip: I loved my stay in the Chesapeake room with the Private bath. It was in the front upstairs and was...
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  • Stayed April 2014, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Limerick, Pennsylvania
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed November 11, 2013

Once again, the Widow's Walk Inn was the perfect "base camp" for our Eastern Shore (2-night) weekend getaway with friends that included the Easton "Waterfowl Festival" nearby. The third visit to this B&B for my wife and I ... and as always, we were well cared for by Innkeepers Bob & Susan. Breakfast was thoughtfully prepared fresh each morning; bed was great, everything was tidy and well cared for. It's location near community park, shops, and gallery's makes for wonderful, casual strolls. Great suggestions for local dining were provided along with Bob's take on the latest happenings in and around Chestertown, MD ... our adopted "home town" destination.

Room Tip: Ground floor worked best for me since I have respiratory issues ... very accommodating.
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  • Stayed November 2013, traveled with friends
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Annapolis, Maryland
Senior Contributor
33 reviews 33 reviews
12 hotel reviews
Reviews in 17 cities Reviews in 17 cities
28 helpful votes 28 helpful votes
5 of 5 stars Reviewed September 24, 2013

My first visit to a bed and breakfast and if this is the treatment you get, I'll take a B&B ANY day over an impersonal hotel! The property is lovely with a private drive and parking behind the house. Rooms are very spacious and nicely decorated. It was the annual Fall Family weekend for Washington College and the house was full of awesome people.

And then there's Bob... I can't say a bad word about him. He is a wonderful person/character and to our enjoyment, he told us a great deal about the town and the history of several stores and buildings. He makes a wonderful breakfast and will give an honest opinion of any place in town you're thinking of visiting. He is very good-natured in his humor and he has plenty of it. Though we only saw Sue briefly, she's a lovely, warm woman and God bless her for taking such good care of Bob!

  • Stayed September 2013, traveled with family
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
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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