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Chestertown

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Map of Chestertown Hotels

Hotels (2)

B&Bs / Inns (12)

Specialty Lodging (0)

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25227 Chestertown Road, Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
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$216 - $294 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (126)
Special Offer Save $50 on Summer...
10568 Cliff Rd, Chestertown, MD 21620
Great Oak Manor Slideshow
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$190 - $286 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
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208 Mount Vernon Ave, Chestertown, MD
$99 - $139 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
Traveler photos (19)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$94 - $206 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Great Stay 
  • Friendly staff, very clean, modern, and well furnished rooms. The free... more
  • July 13, 2016
Professional photos | Traveler photos (29)
Special Offer Book Direct and Save
8796 Maryland Pkwy., Chestertown, MD 21620
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
Traveler photos (30)
Special Price 2nd night 1/2 off!
402 High St., Chestertown, MD 21620
$30 - $135 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
  •  Happy Wife, Good Life 
  • Is but a bit of wisdom from our innkeeper. We enjoyed our stay, the good... more
  • June 11, 2016
Traveler photos (3)
114 Washington Ave, Chestertown, MD 21620
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$193 - $244 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
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231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 12 B&Bs / Inns in Chestertown
  •  Severely lacking... 
  • The entrance was not clearly marked. I had an elderly companion walking... more
  • July 19, 2016
Traveler photos (2)
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
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$87 - $190 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Professional photos | Traveler photos (28)
Special Offer Choice Privileges Points
1008 Rolphs Wharf Road, Chestertown, MD 21620
Ollie #8 of 12 B&Bs / Inns in Chestertown
160 Claddaugh Lane, Chestertown, MD 21620
$75 - $95 Avg. price/night*
Ollie #9 of 12 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)
954 High Street, Chestertown, MD 21620
Ollie #10 of 12 B&Bs / Inns in Chestertown
  •  Faded Glory 
  • Four "tall ships" were going to be in Chestertown, Maryland, for the... more
  • November 23, 2013
Traveler photos (3)
609 Washington Avenue, Chestertown, MD 21620
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$62 - $85 Avg. price/night*
Ollie #11 of 12 B&Bs / Inns in Chestertown
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208 High Street, Chestertown, MD 21626