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.
Book On TripAdvisor Bonus Book your hotel on TripAdvisor — then save 20% on things to do for your trip. Use code BOOKTOSAVE.

“Agree that Bob is wonderful!” 5 of 5 stars
Review of Widow's Walk Inn

Widow's Walk Inn
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Chestertown
Check In mm/dd/yyyy Check Out mm/dd/yyyy
Widow's Walk Inn
Save
You added Widow's Walk Inn to your Saves list
Ranked #5 of 12 Chestertown B&B and Inns
Columbus, Ohio
2 reviews
“Agree that Bob is wonderful!”
5 of 5 stars Reviewed June 2, 2013

I can't understand why anyone would bash Bob because he's awesome. I visited Chestertown for business and stayed with Bob and Susan at the Widow's Walk for 2 days. Bob was charming and delightful! The B&B itself is lovely and well-cared for. Bob is a great cook and made us a fabulous souffle for breakfast. He could not have been more accomodating. He and Susan gave me their personal cell phone to call when I got to Chestertown as I'd never been there before and they wanted me to feel welcome and not get lost when driving at night. I give this B&B my highest marks!!!

  • Stayed April 2013, traveled on business
    • 5 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
Thank Nicole S
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

38 reviews from our community

Traveler rating
    31
    6
    0
    1
    0
See reviews for
16
10
2
5
Rating summary
  • Location
  • Sleep Quality
  • Rooms
  • Service
  • Value
  • Cleanliness
Traveler tips help you choose the right room.   Room tips (8)
Date | Rating
  • English first
  • Any
English first
New Hope, Pennsylvania
Level Contributor
4 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed February 4, 2013

There are a lot of us out there that need to take deep breath when writing these reviews. We have stayed with Bob three times now and plan to stay another 3-4 times while our son completes his degree at nearby Washington College. There is very private off street parking, a great front porch with rockers, etc to sit outside with a beer or glass of wine. Walking to local great restaurants is a joy.
Take 5 minutes to get to know Bob and you will be back whenever in the area. If you are visiting Washington College its a great change of pace from the "big box" hotel chains on the other side of town and maybe a 2-3 minute drive once you find the back way to school. We travel a lot and have had some real bad experiences with B&B's but Widow's Walk is great.

  • Stayed September 2012, traveled with family
    • 4 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
1 Thank Stephen F
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Jacksonville, Florida
Level Contributor
2 reviews
common_n_hotel_reviews_1bd8 4 helpful votes
2 of 5 stars Reviewed November 30, 2012

Bob is a bully. Bob is the innkeeper and I found his attitute to be abusive. I was shocked the first morning at his disparaging and unfounded imitation of my response to the question what did I want in my coffee. My response was "Cream. Or half and half. Or milk." My response was intended to indicate flexibility. My response was greeted with silence, and then he repeated "What do you want in your coffee?" I thought he was perhaps hard of hearing and didn't want to embarrass him, but said "Did you not hear my answer?" He said " Well, I heard I'll have mah, mah, mah, mah, mah," pulling the corners of his mouth down and wobbling his head as he engaged in his parody of me. He did it when it when we were alone in the kitchen. No witnesses. Typical bullying behavior. At breakfast the next day, I heard one of the guests who had stayed there before tell one of the new guests (both males) if you don't mind the abuse this was a great B&B. Bob also came into my room while my sister and I were out for the day. I know because he folded the towel I had opened up to dry on the rod on the back of the door. When we got back, it was folded in thirds and still wet. He also folded my shirt that I had spread open on top of my suitcase to prevent wrinkling. I know innkeepers the rooms to take out the trash, but I found his handling of my personal items intrusive. I would advise you to take a pass on The Widow's Walk.

  • Stayed August 2012, traveled with family
    • 3 of 5 stars
      Value
    • 3 of 5 stars
      Location
    • 3 of 5 stars
      Sleep Quality
    • 3 of 5 stars
      Rooms
    • 3 of 5 stars
      Cleanliness
    • 3 of 5 stars
      Service
Helpful?
4 Thank renegade499
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Newtown, Connecticut
Level Contributor
6 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
5 of 5 stars Reviewed May 24, 2012

My wife and I had another wonderful weekend at the Widows Walk this past weekend. Bob and Susan as usual provided great conversation and advice on the local life of the historic port town.
I think what we love most is the ability to park the car in the hidden parking area of the Inn and then walk to any one of four great restaurants, art galleries, shops and of course the river front.
We've been coming here for four years now and will plan on coming down again soon.

  • Stayed May 2012, traveled as a couple
    • 5 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
1 Thank PeterO293
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
VA
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed October 14, 2011

Had a wonderful weekend in Chestertown. Our stay at Widow's walk was just fantastic, walking distance to great restaurants and shops. Bob and Sue are just charming and great hosts, both of them have great sense of humor and they really make you feel at home. You will not be disappointed if you choose "Widow's walk" when you go to Chestertown or if you make it a rest stop on your way to visiting other places. Book early as the inn gets filled up quickly. :) N.M

  • Stayed October 2011, traveled with friends
    • 5 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
1 Thank Nick N
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Fairfax, Virginia
1 review
5 of 5 stars Reviewed October 12, 2011

Just returned from a week-end in Chestertown and stayed at the Widow's Walk. While we enjoyed our time in Chestertown and Rock Hall, our stay at this Bed and Breakfast made the difference. It really felt like home away from home. The place is immaculate, inside and outside. The interior design/decor is fabulous, yet cozy and inviting. Our room was impeccable not to mention super comfortable. Breakfast there is a classy affair in a lovely dining room with lovely china, and yes the much mentioned Blueberry French Toasts is quite a highlight. The best part of the place lies in the warmth and super friendly hosts Bob and Sue who use their delightful sense of humor to make their guests' stay a pleasant, fun and memorable one. The location is perfect within walking distance to fine restaurants and shops. We will be back and you should definitely check it out.

  • Stayed October 2011, traveled with friends
    • 5 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 4 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
Thank rc-1007
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Bethesda, Maryland
1 review
5 of 5 stars Reviewed September 27, 2011

Widow's Walk Inn in Chestertown, MD, is a wonderful, relaxing B & B with very hospitable hosts.The best part of all was the Saturday morning breakfast of baked Blueberry French Toast which is to die for. You must request it! I am a breakfast lover and this is by far one of the best breakfast dishes I've ever had. Enjoy the beautiful historic inn and the delish breakfasts!

  • Stayed September 2011, traveled with family
    • 5 of 5 stars
      Value
    • 5 of 5 stars
      Location
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Rooms
    • 5 of 5 stars
      Cleanliness
    • 5 of 5 stars
      Service
Helpful?
Thank ncr_11
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Hotels you might also like...
Also consider these accommodations in or near Chestertown
1.2 mi away
Holiday Inn Express Hotel & Suites Chestertown
1.2 mi away
Comfort Suites
Comfort Suites
#2 of 2 in Chestertown
4.0 of 5 stars 101 reviews
19.3 mi away
Hilton Garden Inn Kent Island
Show Prices
Show Prices
Show Prices
1.4 mi away
Brampton Bed and Breakfast Inn
0.2 mi away
John Stam House
John Stam House
#6 of 12 in Chestertown
5.0 of 5 stars 21 reviews
8.1 mi away
Great Oak Manor
Great Oak Manor
#2 of 12 in Chestertown
5.0 of 5 stars 290 reviews
Show Prices
Show Prices
Show Prices

Been to Widow's Walk Inn? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Widow's Walk Inn

Property: Widow's Walk Inn
Address: 402 High St., Chestertown, MD 21620
Location: United States > Maryland > Chestertown
Amenities:
Hotel Style:
Ranked #5 of 12 B&Bs / Inns in Chestertown
Price Range (Based on Average Rates): $
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