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All 12 Chestertown B&Bs / inns

Widow's Walk Inn

402 High St., Chestertown, MD 21620
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Ranked #4 of 12 Chestertown B&B and Inns
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23 people have reviewed this hotel

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Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    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 (6)
Date | Rating
  • English first
  • Any
English first
East Troy, WI
Senior Contributor
25 reviews 25 reviews
10 hotel reviews
15 helpful votes 15 helpful votes
4 of 5 stars Reviewed June 23, 2014

Widow's Walk Inn B and B is a very good place to stay if ever you find yourself in Chestertown. It is very conveniently located - close to downtown, the river - and provides ample off street parking. The inn is an 1870s vintage home and although Victorian is not my preferred style, it was very interesting and comfortable. Our... More

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Baltimore, Maryland
Top Contributor
58 reviews 58 reviews
14 hotel reviews
67 helpful votes 67 helpful votes
5 of 5 stars Reviewed June 21, 2014

I do not mean to take away anything from the Widow's Walk when I say that my wife and I usually go to the Brampton Inn when we come to Chestertown. We enjoy the whole package there - the rooms, the breakfast, the front porch, the grounds, the opportunity to take long walks across the highway, the lantern atop the... More

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Palm Springs, California
1 review
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... More

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Whippany, New Jersey
2 reviews
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... More

Was this review helpful? Yes 1
Lexington Park, Maryland
2 reviews
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.

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Frederick, Maryland
Senior Reviewer
7 reviews 7 reviews
4 hotel reviews
5 helpful votes 5 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... More

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Hagerstown, Maryland
2 reviews
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,... More

Was this review helpful? Yes 1
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... More

Was this review helpful? Yes 1
Annapolis, Maryland
Senior Contributor
32 reviews 32 reviews
11 hotel reviews
26 helpful votes 26 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... More

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Columbus, Ohio
2 reviews
5 of 5 stars Reviewed June 2, 2013

I can't understand why anyone would bash Bob because he's awesome. I visited Chestertown for business and stayed with Bob and Susan at the Widow's Walk for 2 days. Bob was charming and delightful! The B&B itself is lovely and well-cared for. Bob is a great cook and made us a fabulous souffle for breakfast. He could not have been... More

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Additional Information about Widow's Walk Inn

Address: 402 High St., Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Hotel Style:
Ranked #4 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $

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