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.

“Another wonderful weekend at the Widow.” 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
402 High St., Chestertown, MD 21620   |  
Hotel amenities
Ranked #6 of 12 Chestertown B&B and Inns
Newtown, Connecticut
Level Contributor
6 reviews
common_n_hotel_reviews_1bd8 2 helpful votes
“Another wonderful weekend at the Widow.”
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
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Write a Review

31 reviews from our community

Traveler rating
    26
    4
    0
    1
    0
See reviews for
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
Traveler tips help you choose the right room.   Room tips (8)
Date | Rating
  • English first
  • Any
English first
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
Was this review helpful? Yes 1
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
Was this review helpful? Yes
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
Was this review helpful? Yes
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 September 12, 2011

We've been staying with Bob and Sue for the last four years. The Widows Walk is beautiful inside and out with huge, comfortable rooms. I get up early to chat with Bob every morning and catch up on Chestertown news. Breakfast is wonderful and, Bob will kill me, but ask for the' blueberry puffs - incredible.

Room Tip: Cheasapeak is great.
See more room tips
  • Stayed August 2011, traveled with family
    • 4 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Lutherville Timonium
Level Contributor
10 reviews
4 hotel reviews
common_n_hotel_reviews_1bd8 5 helpful votes
4 of 5 stars Reviewed August 1, 2011

Widow's Walk was not our first choice but will be from now on. A great Victorian house and a wonderful host in Bob. Just ignore his teasing! We looked online at others which were not available midweek in the summer so ended up at Widow's Walk and are so glad. It was in walking distancce of everything but not in the middle of the bustle. The air conditioner was a little undersized for the size of the room, but most people would be fine using the overhead fan. Just turn the temp. lower than you expect. It was 100 degrees when we were there and we were comfortable. Widow's Walk is less pretentious than some but the price is right and Bob makes a great breakfast. Since about an hour and 45 min. from Baltimore, we decided it will be our getaway when we just need to relax.

  • Stayed July 2011, traveled as a couple
    • 4 of 5 stars Value
    • 4 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 1
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Pittston, Pennsylvania
2 reviews
common_n_hotel_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed June 26, 2011

My husband and I spent Memorial Day weekend at the Widow's Walk Inn in Chestertown, MD and have already been talking about returning. We have stayed in many B & B's and Inn's and this is by far one of our favorites. The Inn itself is a beautiful Victorian in an excellant location on High Street which is a quick stroll to town restaurants, and the waterfront. The property is kept absolutely immaculate inside and out, and is furnished with beautiful antiques. The Inn Keepers, Bob and Susan were extremely helpful prior to our trip with information on restaurants, and suggestions about the weekend. Breakfast each day was not only delicious but very entertaining. Bob's talent in the kitchen is obvious with the breakfasts that we shared each morning. We have never stayed at a B & B and felt so at home and felt so comfortable.

  • Stayed May 2011, traveled as a couple
    • 5 of 5 stars Value
    • 5 of 5 stars Sleep Quality
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
mm/dd/yyyy mm/dd/yyyy
Price Your Stay
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 91 reviews
19.3 mi away
Hilton Garden Inn Kent Island
Show Prices
Show Prices
Show Prices
18.7 mi away
Sleep Inn
Sleep Inn
#3 of 5 in Grasonville
4.0 of 5 stars 103 reviews
1.4 mi away
Brampton Bed and Breakfast Inn
0.2 mi away
John Stam House
John Stam House
#4 of 12 in Chestertown
5.0 of 5 stars 15 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

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

Owners: What's your side of the story?

If you own or manage Widow's Walk Inn, register now for free tools to enhance your listing, attract new reviews, and respond to reviewers.