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Chestertown

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Map of Chestertown Hotels

Hotels (2)

B&Bs / Inns (11)

Specialty Lodging (0)

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25227 Chestertown Road, Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
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$255 - $277 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (122)
Offers & Announcements $25 off room rate
208 Mount Vernon Ave, Chestertown, MD
$99 - $139 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns in Chestertown
  •  Great Stay! 
  • Cheryl and David run a sweet, class-act, comfortable establishment. There... more
  • January 9, 2016
Traveler photos (19)
10568 Cliff Rd, Chestertown, MD 21620
Great Oak Manor Slideshow
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$175 - $244 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (122)
Special Offer Midweek BOGO Special!
8796 Maryland Pkwy., Chestertown, MD 21620
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
Traveler photos (29)
Special Price BOGO Sun-Thur
114 Washington Ave, Chestertown, MD 21620
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$193 - $244 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (9)
402 High St., Chestertown, MD 21620
$30 - $135 Avg. price/night*
Ollie #6 of 11 B&Bs / Inns in Chestertown
Traveler photos (3)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 11 B&Bs / Inns in Chestertown
  •  Lovely historic inn 
  • We loved the decor and all the common areas, the inn is kept up very... more
  • October 18, 2015
Traveler photos (2)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$106 - $189 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (30)
Special Offer Save 10-30%
1008 Rolphs Wharf Road, Chestertown, MD 21620
Ollie #8 of 11 B&Bs / Inns in Chestertown
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
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$97 - $155 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Great place to stay 
  • We were very pleased with our stay. We stayed here while attending a... more
  • October 21, 2015
Professional photos | Traveler photos (28)
Special Offer Choice Privileges Points
954 High Street, Chestertown, MD 21620
Ollie #9 of 11 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)
160 Claddaugh Lane, Chestertown, MD 21620
$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)
609 Washington Avenue, Chestertown, MD 21620
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$62 - $85 Avg. price/night*
Ollie #11 of 11 B&Bs / Inns in Chestertown
  •  No way stay away 
  • This hotel was not that great a few years ago but this year hit rock... more
  • August 10, 2015
Professional photos | Traveler photos (8)