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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 Rd, Chestertown, MD 21620-3944
Brampton Bed and Breakfast Inn Slideshow
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$237 - $316 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
  •  Relax to the max 
  • I loved my stay here. It was for my first anniversary. We stayed in... more
  • September 22, 2016
Professional photos | Traveler photos (126)
Offers & Announcements Fall Retreat & Refresh
10568 Cliff Rd, Chestertown, MD 21620-4115
Great Oak Manor Slideshow
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$175 - $296 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (158)
Special Offer Buy One Get One FREE
208 Mount Vernon Ave, Chestertown, MD 21620-1324
$99 - $139 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
Traveler photos (19)
150 Scheeler Rd, Chestertown, MD 21620-1031
Holiday Inn Express Hotel & Suites Chestertown Slideshow
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$100 - $211 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (29)
Special Offer Book Direct and Save
8796 Maryland Pkwy, Chestertown, MD 21620-4209
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
Traveler photos (30)
402 High St, Chestertown, MD 21620-1312
No photo provided
$30 - $135 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
114 Washington Ave, Chestertown, MD 21620-1616
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$193 - $244 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (13)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #7 of 12 B&Bs / Inns in Chestertown
  •  Summer memories 
  • This is our second stay at The River Inn. We stayed at another B&B but our... more
  • August 23, 2016
Traveler photos (12)
231 High St, Chestertown, MD 21620-1517
$30 - $180 Avg. price/night*
Ollie #8 of 12 B&Bs / Inns in Chestertown
  •  Disappointing at best 
  • Disappointing. Expensive. Worst breakfast in our B&B experience. They... more
  • September 12, 2016
Traveler photos (2)
208 High St, Chestertown, MD 21620-1518
Ollie #9 of 12 B&Bs / Inns in Chestertown
160 Claddaugh Ln, Chestertown, MD 21620-2311
$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)
160 Scheeler Rd, Chestertown, MD 21620
Quality Suites Slideshow
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$91 - $199 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Parents Weekend Visit 
  • We arrived prior to noon at the hotel and asked for a first floor room... more
  • September 23, 2016
Professional photos | Traveler photos (28)
Special Offer Choice Privileges Points
954 High St, Chestertown, MD 21620-3955
Ollie #11 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 Ave, Chestertown, MD 21620-1219
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$62 - $91 Avg. price/night*
Ollie #12 of 12 B&Bs / Inns in Chestertown
  •  Unkept 
  • I should have known, when we saw no cars in the parking lot. It looked... more
  • August 9, 2016
Professional photos | Traveler photos (8)