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Widow's Walk Inn

402 High St., Chestertown, MD 21620
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29 reviews from our community

Traveler rating
    24
    4
    0
    1
    0
See reviews for
10
7
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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    (29)
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    (5)
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    (10)
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    (12)
  • Dec-Feb only
    (2)
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Annapolis, Maryland
Senior Contributor
39 reviews 39 reviews
6 hotel reviews
10 helpful votes 10 helpful votes
4 of 5 stars Reviewed 1 week ago

Widow's Walk Inn is a traditional bed-and-breakfast decorated in the Victorian era in charming Chestertown, Maryland. The hosts are knowledgeable about where to eat and provided us with stories of interest. Kayaking at the public boat ramp was easily accessible by the marina and there was no boat traffic at all.

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Gainesville, Virginia
Senior Reviewer
10 reviews 10 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed November 15, 2014

Lovely place. Very clean and comfortable. Robert, our host, was very nice and wanted to make sure we had a good stay. You can walk to the stores and restaurants. No tv's in rooms so if that is important, you will miss that amenity.

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Hanover, New Hampshire
Contributor
13 reviews 13 reviews
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed November 8, 2014

We spent three nights here and could not have chosen a better location with a very engaging owner, Bob. Three elegant breakfasts, non-stop conversations with a wide range of fellow visitors, capped off each morning with puny humor supplied by Bob. Definitely should be on the top of your list of where to stay in Chestertown!

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Wallingford, CT
Reviewer
4 reviews 4 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed October 1, 2014

My husband and I spent two nights at The Widows Walk while attending Washington College Fall Family weekend. We decided to stay at a B&B this time because many times in the area we stayed at hotels in the area that we just got tired of that hotel "scene" and wanted something better. Which The Widows Walk was all of... More 

Was this review helpful? Yes 1
Jefferson, Maryland
1 review
5 of 5 stars Reviewed September 22, 2014

My husband and I stayed at Widow's Walk B&B for Family weekend at Washington College. We stayed in the Maryland room, which is on the main floor. The room was spacious, clean and authentically decorated for this Victorian home. Even though the B&B is located on the main street of Chestertown, it provides a quite refuge. Widow's Walk is conveniently... More 

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Columbia, Maryland
Reviewer
3 reviews 3 reviews
5 of 5 stars Reviewed August 24, 2014

This was the first time my fiancee and I visited Chesterstown. We chose the Widow's Walk Inn quite by accident since most of the other B&B's were already booked. Needless to say, I am glad that we were able to get reservations at this wonderful B&B. The owner, Bob, made us feel comfortable and was a wealth of knowledge about... More 

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East Troy, WI
Senior Contributor
32 reviews 32 reviews
13 hotel reviews
17 helpful votes 17 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 

Was this review helpful? Yes 1
Baltimore, Maryland
Top Contributor
80 reviews 80 reviews
16 hotel reviews
105 helpful votes 105 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

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