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

Refine search

Price per night

 

Traveler rating

 

Hotel class

 

Property name

Reset
 
Free Newsletter

Interested in Chestertown?

We'll send you updates with the latest deals, reviews and articles for Chestertown each week.

Map of Widow's Walk Inn

Hotels (2)

B&Bs / Inns (11)

Specialty Lodging (0)

You are zoomed out too far to see location pins. Please zoom back in.
Search hotels
Map showing X-Y of Z
Clear filter(s)

Hotels Travelers Trust

Sort by [ Popularity ] [ Price ]
25227 Chestertown Rd., Chestertown, MD 21620-3944
Show Prices
$220 - $347 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (161)
Great Oak Manor (Chestertown, MD)
10568 Cliff Rd, Chestertown, MD 21620-4115
Show Prices
$186 - $314 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns in Chestertown
  •  Great is Great 
  • The setting, the staff, and of course the Manor are all great. If you need... more
  • September 17, 2017
Professional photos | Traveler photos (190)
Simply Bed and Bread (Chestertown, MD)
208 Mount Vernon Ave, Chestertown, MD 21620-1324
$99 - $139 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
Traveler photos (20)
The Inn at Mitchell House (Chestertown, MD)
8796 Maryland Pkwy, Chestertown, MD 21620-4209
Show Prices
$165 - $166 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
Traveler photos (37)
150 Scheeler Rd, Chestertown, MD 21620-1031
Show Prices
$102 - $248 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Problems at front desk 
  • I've waited awhile to do this review because I wanted to be fair & I was... more
  • September 6, 2017
Professional photos | Traveler photos (29)
John Stam House (Chestertown, MD)
114 Washington Ave, Chestertown, MD 21620-1616
Show Prices
$209 - $244 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
Traveler photos (15)
Widow's Walk Inn (Chestertown, MD)
402 High St., Chestertown, MD 21620-1312
No photo provided
$30 - $135 Avg. price/night*
Ollie #6 of 11 B&Bs / Inns in Chestertown
  •  Smitten 
  • Make the Widow's Walk Inn your home away from home in Chestertown! The... more
  • August 27, 2017
White Swan Tavern (Chestertown, MD)
231 High St, Chestertown, MD 21620-1517
$30 - $180 Avg. price/night*
Ollie #7 of 11 B&Bs / Inns in Chestertown
Traveler photos (63)
The Imperial (Chestertown, MD)
208 High St, Chestertown, MD 21620-1518
Ollie #8 of 11 B&Bs / Inns in Chestertown
The River Inn (Chestertown, MD)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #9 of 11 B&Bs / Inns in Chestertown
  •  Summer memories 
  • This is our second stay at The River Inn. We stayed at another B&B but our... more
  • August 23, 2016
Traveler photos (12)
160 Claddaugh Ln, Chestertown, MD 21620-2311
$75 - $95 Avg. price/night*
Ollie #10 of 11 B&Bs / Inns in Chestertown
  •  Nice Stay 
  • Whilst browsing I noted no reviews in last several years so I'll add one... more
  • August 24, 2011
Traveler photos (1)
Quality Suites (Chestertown, MD)
160 Scheeler Rd., Chestertown, MD 21620-1031
Show Prices
$87 - $189 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Traveler photos (46)
Driftwood Inn (Chestertown, MD)
609 Washington Avenue, Chestertown, MD 21620
No photo provided
Show Prices
$63 - $118 Avg. price/night*
Ollie #11 of 11 B&Bs / Inns in Chestertown
  •  Good basic motel. 
  • Management is friendly, and you can tell they are upgrading and improving... more
  • September 5, 2017
Professional photos | Traveler photos (8)

Additional Widow's Walk Inn Information

5.0 of 5 bubbles | 40 Reviews
Price range (per night): $63 - $118