We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Widow's Walk Inn

Save
Book on TripAdvisor
Trusted partner. We work with to make your booking as easy as possible.
Secure payments. We use industry-leading practices to keep your information secure.
Enter dates for best prices
powered by PriceFinder
Prices from our online travel partners are not available
We can't find prices for this hotel
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In Check Out
Show Prices
View Map
{"widget":{"name":"ibex_photo_carousel","template":"ibex_photo_carousel__widget","dust":{"nav_controls":"ibex_photo_carousel__nav_controls"},"divClasses":"prw_rup prw_ibex_photo_carousel","js":{"handlers":"(ta.prwidgets.getjs(this,'handlers'))"},"moduleList":["handlers"]},"scriptFlags":null,"containerClass":null}
Add Photo Write a Review

39 Reviews from our TripAdvisor Community

Traveller rating
Traveller type
Time of year
Language
There are newer reviews for Widow's Walk Inn
See the most recent reviews
Showing 39: English reviews
Annapolis, Maryland
Reviewed 15 May 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.

 Report
Helpful?
Thank kmeister5
Gainesville, Virginia
Reviewed 15 November 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.

 Report
Helpful?
Thank BritishgalfromUSA
Hanover, New Hampshire
Reviewed 8 November 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!

 Report
Helpful?
Thank brstefany
Wallingford, CT
Reviewed 2 October 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...

 Report
Helpful?
1Thank Chuck S
Jefferson, Maryland
Reviewed 23 September 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...

 Report
Helpful?
Thank Paula B
Columbia, Maryland
Reviewed 25 August 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...

 Report
Helpful?
Thank Scarlettstar57
East Troy, WI
Reviewed 23 June 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...

 Report
Helpful?
1Thank Bassplayer13
Frederick, Maryland
Reviewed 21 June 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...

 Report
Helpful?
Thank StillSteppinOut
Palm Springs, California
Reviewed 12 June 2014 via mobile

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...

 Report
Helpful?
Thank Stephen S
Whippany, New Jersey
Reviewed 7 June 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...

 Report
Helpful?
1Thank NJtraveler1990

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Amenities

Highlights
  • Free Parking
In your room
  • Air Conditioning
Services
  • Free Parking

Additional Information about Widow's Walk Inn

Address: 402 High St., Chestertown, MD 21620-1312
Region: United States > Maryland > Chestertown
Price Range: RM134 - RM601 (Based on Average Rates for a Standard Room)
Number of rooms: 6

Is This Your TripAdvisor Listing?

Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more.

Claim Your Listing

Questions & Answers

Questions? Get answers from Widow's Walk Inn staff and past guests.
Posting guidelines
Typical questions asked:
  • Can tickets for local attractions be purchased at the front desk?
  • Do you have to pay extra for a mini-fridge?
  • At what time does the pool open each day?