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Widow's Walk Inn

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

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South Burlington, Vermont
Level Contributor
142 reviews
25 hotel reviews
common_n_hotel_reviews_1bd8 77 helpful votes
4 of 5 stars Reviewed 4 weeks ago

The Innkeepers, Bob and Susan, certainly made our visit enjoyable. The breakfasts were very good and Bob never met a good joke that he didn't like (or a bad one for that matter). The Inn is in the center of the town and in walking distance from several good restaurants. We had three rooms and the Inn to ourselves. The... More 

Thank gregv_ma
Nashville, Tennessee
Level Contributor
38 reviews
17 hotel reviews
common_n_hotel_reviews_1bd8 14 helpful votes
4 of 5 stars Reviewed August 19, 2015

Just a few blocks from the river. We were able to walk to restaurants and shops. Our room (downstairs) was spacious and comfortable. Great mattress. Our host was entertaining. And the breakfast was delicious.

Thank D B
County Dublin, Ireland
2 reviews
5 of 5 stars Reviewed July 27, 2015

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.

Thank Timothy E
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed July 16, 2015 via mobile

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 

Thank Michael K
Annapolis, Maryland
Level Contributor
40 reviews
7 hotel reviews
common_n_hotel_reviews_1bd8 8 helpful votes
4 of 5 stars Reviewed May 14, 2015 via mobile

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.

Thank kmeister5
Gainesville, Virginia
Level Contributor
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.

Thank BritishgalfromUSA
Hanover, New Hampshire
Level Contributor
15 reviews
common_n_hotel_reviews_1bd8 6 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!

Thank brstefany
Wallingford, CT
Level Contributor
11 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 

1 Thank Chuck S
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 

Thank Paula B
Columbia, Maryland
Level Contributor
6 reviews
3 hotel 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 

Thank Scarlettstar57
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