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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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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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$247 - $292 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (81)
Offers & Announcements Special Rate $200/night
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 50% off room rate
402 High St., Chestertown, MD 21620
No photo provided
$30 - $135 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
  •  A good stay 
  • My husband and I spent two nights at The Widows Walk while attending... more
  • October 1, 2014
10568 Cliff Rd, Chestertown, MD 21620
$165 - $310 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
  •  Most excellent 
  • Stayed at the Great Oak for 3 nights on Womantours Maryland Eastern Shore... more
  • October 11, 2014
Traveler photos (64)
114 Washington Ave, Chestertown, MD
Ollie #6 of 12 B&Bs / Inns in Chestertown
  •  Lovely Lovely Lovely 
  • Lovely Victorian B&B - about midway between High Street and Mary... more
  • October 21, 2014
Traveler photos (1)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 12 B&Bs / Inns in Chestertown
  •  Peace and Serenity 
  • Very comfortable stay in this impeccably restored 18th century inn in the... more
  • September 28, 2014
Traveler photos (2)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$101 - $199 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Good for a few days 
  • We went to Chestertown for a family wedding and stayed here. A bit hard... more
  • October 15, 2014
Professional photos | Traveler photos (27)
Special Offer Save on Hotel Packages!
1008 Rolphs Wharf Road, Chestertown, MD 21620
Ollie #8 of 12 B&Bs / Inns in Chestertown
  •  Heads above the rest! 
  • My husband, mother-in-law, our two dogs and I had a(nother) excellent... more
  • June 27, 2014
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
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$85 - $177 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Ok place 
  • AC wasn't working. It got very warm, we had to open the window. The room... more
  • October 19, 2014
Professional photos | Traveler photos (14)
Special Offer Choice Privileges Points
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 (1)
609 Washington Avenue, Chestertown, MD 21620
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$56 - $72 Avg. price/night*
Ollie #11 of 12 B&Bs / Inns in Chestertown
  •  Worst motel ever. 
  • I'm still traumatized by this place. If there were any other places to... more
  • July 7, 2014
Professional photos | Traveler photos (8)
108 Spring Ave, Chestertown, MD 21620