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Widow's Walk Inn

402 High St., Chestertown, MD 21620
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32 Reviews from our TripAdvisor Community

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Traveler rating
    26
    5
    0
    1
    0
See reviews for
11
9
2
5
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 (8)
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    (32)
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    (5)
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    (13)
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There are newer reviews for Widow's Walk Inn
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Baltimore, Maryland
Level Contributor
81 reviews
16 hotel reviews
common_n_hotel_reviews_1bd8 101 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 

Was this review helpful? Yes
Palm Springs, California
2 reviews
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
common_n_hotel_reviews_1bd8 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
Level Contributor
6 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
Level Contributor
11 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 4 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
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
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
common_n_hotel_reviews_1bd8 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
Level Contributor
37 reviews
14 hotel reviews
common_n_hotel_reviews_1bd8 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 

Was this review helpful? Yes
New Hope, Pennsylvania
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 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 

Was this review helpful? Yes 1
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Amenities