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Chestertown

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Map of Chestertown Hotels

Hotels (3)

B&Bs / Inns (12)

Specialty Lodging (0)

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208 Mount Vernon Ave, Chestertown, MD
$99 - $139 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
Traveler photos (16)
25227 Chestertown Road, Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
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$274 - $276 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (81)
Offers & Announcements Book Direct for Best...
8796 Maryland Pkwy., Chestertown, MD 21620
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
Traveler photos (26)
Offers & Announcements April Weekday Getaway
10568 Cliff Rd, Chestertown, MD 21620
$165 - $310 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
Traveler photos (52)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
Traveler photos (2)
402 High St., Chestertown, MD 21620
$30 - $135 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
Traveler photos (1)
114 Washington Ave, Chestertown, MD
Ollie #7 of 12 B&Bs / Inns in Chestertown
  •  Home Away from Home 
  • A beautifully restored and comfortable Victorian B&B; we enjoyed Marta's... more
  • November 25, 2013
Traveler photos (1)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$104 - $190 Avg. price/night*
Ollie #1 of 3 hotels in Chestertown
  •  Highly recommend! 
  • For many reasons: We had to change our reservation from 2 nights to 1, and... more
  • February 20, 2014
Professional photos | Traveler photos (26)
Special Offer Save on Hotel Packages!
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
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$121 - $165 Avg. price/night*
Ollie #2 of 3 hotels in Chestertown
  •  Eastern Shore Trip 
  • We were visiting the ES to celebrate our anniversary , visit a grandson at... more
  • March 31, 2014
Professional photos | Traveler photos (14)
Special Offer Choice Privileges Points
1008 Rolphs Wharf Road, Chestertown, MD 21620
Ollie #8 of 12 B&Bs / Inns in Chestertown
208 High Street, Chestertown, MD 21620
$95 - $250 Avg. price/night*
Ollie #3 of 3 hotels in Chestertown
  •  Very pleasant stay 
  • My husband and I had such an enjoyable weekend at the imperial hotel. My... more
  • December 11, 2013
Traveler photos (15)
954 High Street, Chestertown, MD 21620
Ollie #9 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)
160 Claddaugh Lane, Chestertown, MD 21620
$75 - $95 Avg. price/night*
Ollie #10 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 (2)
609 Washington Avenue, Chestertown, MD 21620
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$62 - $72 Avg. price/night*
Ollie #11 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (8)
108 Spring Ave, Chestertown, MD 21620