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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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$253 - $288 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
  •  Bramptoninn 
  • My husband and I stayed here as a getaway after our vow ceremony. The... more
  • May 15, 2015
Professional photos | Traveler photos (103)
Offers & Announcements Free Crab Roll Picnic
208 Mount Vernon Ave, Chestertown, MD
$99 - $139 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Traveler photos (18)
114 Washington Ave, Chestertown, MD 21620
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$193 - $219 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (9)
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
  •  Knitting Weekend Fun! 
  • Nine of us were here for a knitting weekend. A couple of the attendees had... more
  • March 17, 2015
Traveler photos (26)
402 High St., Chestertown, MD 21620
No photo provided
$30 - $135 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
  •  Overnight 
  • Widow's Walk Inn is a traditional bed-and-breakfast decorated in the... more
  • May 14, 2015
10568 Cliff Rd, Chestertown, MD 21620
$209 - $222 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
  •  Peaceful and serene 
  • While we didn't spend too much time at the inn, our experience was... more
  • May 8, 2015
Traveler photos (81)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 12 B&Bs / Inns in Chestertown
Traveler photos (2)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$112 - $215 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Just fine 
  • Everyone on staff was extremely friendly, the room was comfortable and the... more
  • April 6, 2015
Professional photos | Traveler photos (30)
Special Offer Save 10-30%
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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$121 - $155 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
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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$62 - $85 Avg. price/night*
Ollie #11 of 12 B&Bs / Inns in Chestertown
  •  Quaint and memorable 
  • It is right on the beach. With pets and sand, the tile floors make sense... more
  • March 18, 2015
Professional photos | Traveler photos (8)
108 Spring Ave, Chestertown, MD 21620