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Widow's Walk Inn

402 High St., Chestertown, MD 21620
Widow's Walk Inn
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31 reviews from our community

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Traveler rating
    26
    4
    0
    1
    0
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11
8
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
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County Dublin, Ireland
2 reviews
5 of 5 stars Reviewed 3 days ago NEW

We enjoyed our stay very much with Inn Keeper Bob & his wife Suzan in their beautiful period house. It was like staying with old friends. Our experience extended beyond Bobs good food to include entertaining conversation & story telling a breakfast time.

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Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed 2 weeks ago

My husband and I stayed here for two nights and loved it. Bob is hilarious with his sarcastic humor and he has a great memory of what you tell him. Bob is a great conversationalist and we enjoyed talking with him about a huge range of topics. I really appreciated his candidness when recommending things to do in the area.... More 

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Annapolis, Maryland
Level Contributor
39 reviews
6 hotel reviews
common_n_hotel_reviews_1bd8 10 helpful votes
4 of 5 stars Reviewed May 14, 2015

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
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10 reviews
common_n_hotel_reviews_1bd8 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
Level Contributor
13 reviews
common_n_hotel_reviews_1bd8 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
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 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 

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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
Level Contributor
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
Level Contributor
33 reviews
13 hotel reviews
common_n_hotel_reviews_1bd8 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 

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Baltimore, Maryland
Level Contributor
81 reviews
16 hotel reviews
common_n_hotel_reviews_1bd8 108 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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