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.

“Staying at Widow's Walk "A must"” 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 11 Chestertown B&B and Inns
VA
1 review
common_n_hotel_reviews_1bd8 1 helpful vote
“Staying at Widow's Walk "A must"”
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.
Write a Review

33 reviews from our community

Traveler rating
Traveler type
Time of year
Language
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.
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
Helpful?
Thank PeterO293
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 6 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
Helpful?
1 Thank eba5
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
Helpful?
Thank JeanM_11
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Leola, Pe
1 review
5 of 5 stars Reviewed June 19, 2011

My husband and I have been staying at the Widow's Walk since 2005. I chose it that year from any number of inns in the area because of its proximity to the shops in Chestertiown, you literally walk out the door and onto the historic streets. We continue to return year after year because the Widow's Walk, has a comfortable and welcoming feel. Whether we're spending quiet time reading or relaxing on the screen porch or find pleasant conversation in the living or dining rooms which, by the way, are appointed with many family furnishings and objects of the inns owners, Bob and Sue, we don't feel "funny" about using the common space as we have in some other bed and breakfasts. The rooms are ALWAYS clean and fresh as well as the bathrooms, and it seems all your need are thought of. The innkeeper is akways available, but doesn't hover. Breakfast is a treat, many times Bob uses fresh produce from local farms. We have found the rates are fair. If you are looking for a consistently comfortable, clean bed and breakfast in a absolutely lovely part of Maryland, this is the place!

Room Tip: Chhose the Susquehanna if you prefer privacy
See more room tips
  • Stayed April 2011, traveled as a couple
    • 4 of 5 stars
      Value
    • 5 of 5 stars
      Sleep Quality
    • 5 of 5 stars
      Cleanliness
    • 4 of 5 stars
      Service
Helpful?
Thank FayeLeola_Pe
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
mm/dd/yyyy mm/dd/yyyy
Show Prices
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 94 reviews
19.3 mi away
Hilton Garden Inn Kent Island
Show Prices
Show Prices
Show Prices
0.2 mi away
John Stam House
John Stam House
#5 of 11 in Chestertown
5.0 of 5 stars 18 reviews
8.1 mi away
Great Oak Manor
Great Oak Manor
#3 of 11 in Chestertown
5.0 of 5 stars 213 reviews
1.4 mi away
Brampton Bed and Breakfast Inn
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 11 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