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All 12 Chestertown B&Bs / inns

Widow's Walk Inn

402 High St., Chestertown, MD 21620
Hotel amenities
Widow's Walk Inn
Ranked #6 of 12 Chestertown B&B and Inns
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17 people have reviewed this hotel

Traveler rating
    14
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    0
    1
    0
See reviews for
6
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2
Rating summary
  • Location
    5 of 5 stars
  • Sleep Quality
    4.5 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 (4)
Date | Rating
  • English first
  • Any
English first
Hagerstown, Maryland
1 review
5 of 5 stars Reviewed 2 days ago NEW

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

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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
29 reviews 29 reviews
10 hotel reviews
20 helpful votes 20 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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New Hope, Pennsylvania
Reviewer
5 reviews 5 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed February 4, 2013

There are a lot of us out there that need to take deep breath when writing these reviews. We have stayed with Bob three times now and plan to stay another 3-4 times while our son completes his degree at nearby Washington College. There is very private off street parking, a great front porch with rockers, etc to sit outside... More

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Jacksonville, Florida
2 reviews
1 helpful vote 1 helpful vote
2 of 5 stars Reviewed November 30, 2012

Bob is a bully. Bob is the innkeeper and I found his attitute to be abusive. I was shocked the first morning at his disparaging and unfounded imitation of my response to the question what did I want in my coffee. My response was "Cream. Or half and half. Or milk." My response was intended to indicate flexibility. My response... More

Was this review helpful? Yes 1
Newtown, Connecticut
Reviewer
5 reviews 5 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed May 24, 2012

My wife and I had another wonderful weekend at the Widows Walk this past weekend. Bob and Susan as usual provided great conversation and advice on the local life of the historic port town. I think what we love most is the ability to park the car in the hidden parking area of the Inn and then walk to any... More

Was this review helpful? Yes 1
VA
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed October 14, 2011

Had a wonderful weekend in Chestertown. Our stay at Widow's walk was just fantastic, walking distance to great restaurants and shops. Bob and Sue are just charming and great hosts, both of them have great sense of humor and they really make you feel at home. You will not be disappointed if you choose "Widow's walk" when you go to... More

Was this review helpful? Yes 1
Fairfax, Virginia
1 review
5 of 5 stars Reviewed October 12, 2011

Just returned from a week-end in Chestertown and stayed at the Widow's Walk. While we enjoyed our time in Chestertown and Rock Hall, our stay at this Bed and Breakfast made the difference. It really felt like home away from home. The place is immaculate, inside and outside. The interior design/decor is fabulous, yet cozy and inviting. Our room was... More

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Bethesda, Maryland
1 review
5 of 5 stars Reviewed September 27, 2011

Widow's Walk Inn in Chestertown, MD, is a wonderful, relaxing B & B with very hospitable hosts.The best part of all was the Saturday morning breakfast of baked Blueberry French Toast which is to die for. You must request it! I am a breakfast lover and this is by far one of the best breakfast dishes I've ever had. Enjoy... 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 #6 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $

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