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All 12 Chestertown B&Bs / inns

Widow's Walk Inn

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402 High St., Chestertown, MD 21620
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Ranked #4 of 12 Chestertown B&B and Inns
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28 reviews from our community

Traveler rating
    24
    3
    0
    1
    0
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10
7
2
5
Rating summary
  • Sleep Quality
    5 of 5 stars
  • Location
    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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Gainesville, Virginia
Senior Reviewer
10 reviews 10 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed 1 week ago

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
11 reviews 11 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed 2 weeks ago

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
3 helpful votes 3 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
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
26 reviews 26 reviews
10 hotel reviews
16 helpful votes 16 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
Top Contributor
64 reviews 64 reviews
16 hotel reviews
73 helpful votes 73 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

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Lexington Park, Maryland
Senior Reviewer
6 reviews 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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Additional Information about Widow's Walk Inn

Address: 402 High St., Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Amenities:
Hotel Style:
Ranked #4 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $
Number of rooms: 6

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