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“Great hospitality and delicious breakfast!” 5 of 5 stars
Review of Widow's Walk Inn

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Widow's Walk Inn
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402 High St., Chestertown, MD 21620   |  
Hotel amenities
Ranked #4 of 12 Chestertown B&B and Inns
Bethesda, Maryland
1 review
“Great hospitality and delicious breakfast!”
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
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24 reviews from our community

Traveler rating
    20
    3
    0
    1
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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 (6)
Date | Rating
  • English first
  • Any
English first
Newtown, Connecticut
Reviewer
5 reviews 5 reviews
Reviews in 3 cities Reviews in 3 cities
2 helpful votes 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.
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  • 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
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Lutherville Timonium
Senior Reviewer
10 reviews 10 reviews
4 hotel reviews
Reviews in 5 cities Reviews in 5 cities
5 helpful votes 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
Reviews in 2 cities Reviews in 2 cities
1 helpful vote 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
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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
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  • 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
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Virginia
Senior Contributor
25 reviews 25 reviews
4 hotel reviews
Reviews in 11 cities Reviews in 11 cities
15 helpful votes 15 helpful votes
5 of 5 stars Reviewed September 16, 2009

I made up my mind to attend the Pirates and Wenches Fantasy Festival in nearby (13 miles away) Rock Hall, MD. Unfortunately, I decided late and could not find a room for a Saturday night close-in Rock Hall. Since I had to pass through Chestertown, MD to get to my destination, I looked at B&B's and hotels there. I decided on the "Widow's Walk Inn" and made reservations by phone. I spoke to Bob, the innkeeper, who said I could check in early on my way to Rock Hall instead of coming back in mid-day at the normal check-in time. This was a big convenience. Upon arrival Bob walked me through the rather large house and pointed out the amenities. I stayed in the Chesapeake Room which is large and tastefully furnished and has an en suite bathroom spacious for a Victorian-era B&B (there are some rooms that have shared facilitties). Returning after a day's worth of festivities, I had a great night's sleep in a very comfortable bed. Breakfast was perfect -- a fresh fruit cup, a variation of french toast, a choice of juice and outstanding coffee. There was no rush to leave and while checking out Bob and his wife Susan spoke about the history of the house and about the attractions in Chestertown. Parking is off-street and the inn is in a quiet neighborhood. The innkeepers are very cordial. I recommend this inn to others and would stay there again.

  • Stayed August 2009, traveled solo
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
    • 5 of 5 stars Service
Was this review helpful? Yes 3
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Greenville, South Carolina
Senior Contributor
25 reviews 25 reviews
17 hotel reviews
Reviews in 21 cities Reviews in 21 cities
24 helpful votes 24 helpful votes
4 of 5 stars Reviewed January 30, 2009

I arrived on a summer weekday & was the only guest, which I gathered was quite common during the week. As the innkeepers live in the carriage house, I had the house to myself... and saw (and heard) the innkeepers only at check-in, and then breakfast 15 hours later.

The house is large, tastefully -- even expensively -- furnished with antiques and semi-antiques. Perhaps too much so, as I felt everything had been arranged "just so" and that it would be bad form to move anything. Certainly a family with children would have to be on tiptoe here.

That said, the room and bath were spacious, comfortable and spotless -- and the price was perfect.

Innkeeper Bob had hot coffee going not long after dawn, and made me a breakfast that lacked for nothing.

The main part of the town is just five minutes walk away -- beautiful town -- and dinner at the Blue Heron is not to be missed.

  • Stayed June 2008, traveled on business
    • 5 of 5 stars Value
    • 5 of 5 stars Location
    • 4 of 5 stars Check in / front desk
    • 5 of 5 stars Rooms
    • 5 of 5 stars Cleanliness
Was this review helpful? Yes 4
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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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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